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Chlorobenzene structure

Chlorobenzene
Chlorobenzene is a monocyclic aromatic compound with one hydrogen atom on the benzene ring substituted with one chlorine. It is produced by chlorination of benzene in the liquid phase with a catalyst. Chlorobenzene is a colourless, flammable liquid with a sweet almond-like odor, at ambient temperature with a relatively high vapour pressure, moderate octanol-water partition coefficient (log 2.8) and moderate to low water solubility (497.9 mg/L @ 25℃). Chlorobenzene has a high solubility in nonpolar solvents, however, it is almost insoluble in water. Technical grade Chlorobenzene is typically 99% pure with < 0.05% benzene and < 0.1% dichlorobenzenes as contaminants. It is a common solvent and a widely used intermediate in the manufacture of other chemicals. Rhodococcus phenolicus is a bacterium species able to degrade chlorobenzene as sole carbon sources. View more+
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1. Names and Identifiers
1.1 Name
Chlorobenzene
1.2 Synonyms
2-Chloroacetic anhydride; Acetic acid,chloro-,anhydride; Benzene, chloro-; Benzenyl chloride; CHLORACETIC ANHYDRIDE; Chlorbenzene; Chloroacetic acid anhydride; Chloroacetic anhydride; Chloroacetyl anhydride; Chlorobenzen; chloro-benzene; CHLOROBENZENE extrapure; CHLOROBENZENE extrapure AR; Chlorobenzene Mono; Chlorobenzene, mono-; Chlorobenzene, Reagent; Chlorobenzenu [Czech]; EINECS 203-628-5; MFCD00000530; Monochlorbenzene; Monochloroacetic acid anhydride; monochloroacetic anhydride; MONOCHLOROBENZENE; monochloro-benzene; monochlorobenzol; PHENYL CHLORIDE; U.N. 1134;
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1.3 CAS No.
108-90-7
1.4 CID
7964
1.5 EINECS
203-628-5
1.6 Molecular Formula
C6H5Cl
1.7 Inchi
InChI=1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H
1.8 InChkey
MVPPADPHJFYWMZ-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC=C(C=C1)Cl
1.10 Isomers Smiles
C1=CC=C(C=C1)Cl
2. Properties
2.1 Vapour pressure
3.86 (vs air)
2.2 Solubility
0.4 g/L (20 oC)
2.3 VaporDensity
3.86 (vs air)
2.4 Appearance
Chlorobenzene appears as a colorless to clear, yellowish liquid with a sweet almond-like odor. Flash point 84°F. Practically insoluble in water and somewhat denser than water (9.2 lb / gal). Vapors heavier than air. Used to make pesticides, dyes, and other chemicals.
2.5 Storage
Ambient temperatures.
2.6 Carcinogenicity
Chlorobenzene was not mutagenic in avariety of bacterial and yeast assays. Existingdata suggest that genotoxicity may not be anarea of concern for chlorobenzene exposure inhumans.
2.7 Chemical Properties
colourless liquid, Chlorination of benzene in the presence of a catalyst (FeCl3 or AICI3) yields chlorobenzene as the first product. Substitution with a second CI yields ortho, para, or meta dichlorobenzene, Eventually all the hydrogens can be substituted to give hexachlorobenzene, C6C16. In the presence ofultraviolet light, the chlorinationofbenzene yields benzene hexachloride, C6H6C~, a derivative ofcyclohexane.
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2.8 Color/Form
APHA: ≤30
2.9 Odor
Faint, not unpleasant odor
2.10 Water Solubility
H2O: 0.4 g/L (20 oC)
2.11 Spectral Properties
Index of refraction: 1.5241 at 20 deg C/D
MAX ABSORPTION (ALCOHOL): 245 NM (LOG E= 1.95); 251 NM (LOG E= 2.34); 258 NM (LOG E= 2.13); 264 NM (LOG E= 2.45)
IR: 5726 (Coblentz Society Spectral Collection)
UV: 6-63 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
Raman: 72 (Dollish et al; Characteristic Raman Frequencies or Organic Compounds. John Wiley & Sons, New York)
1H NMR: 714 (Sadtler Research Laboratories Spectral Collection)
C13 NMR: 153 (Johnson and Jankowski, Carbon-13 NMR Spectra, Jphn Wiley & Sons, New York)
MASS: 61412 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 1586 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
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2.12 Stability
Stable. Incompatible with oxidizing agents. Flammable. Attacks some types of plastics, rubber and coatings.
2.13 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: The simplest member of the class of monochlorobenzenes, that is benzene in which a single hydrogen has been substituted by a chlorine.
3.2 Description

colourless liquid, Chlorination of benzene in the presence of a catalyst (FeCl3 or AICI3) yields chlorobenzene as the first product. Substitution with a second CI yields ortho, para, or meta dichlorobenzene, Eventually all the hydrogens can be substituted to give hexachlorobenzene, C6C16. In the presence ofultraviolet light, the chlorinationofbenzene yields benzene hexachloride, C6H6C~, a derivative ofcyclohexane. Chlorobenzene, also called monochlorobenzene, is a monocyclic aromatic compound


Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

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3.3 Potential Exposure
Chlorobenzene is used in the manufacture of aniline, phenol, and chloronitrobenzene; as an intermediate in the manufacture of dyestuffs and manypesticides, as a solvent; and emulsifier.
3.4 Purification Methods
The main impurities are likely to be chlorinated impurities originally present in the *benzene used in the synthesis of chlorobenzene, and also unchlorinated hydrocarbons. A common purification procedure is to wash it several times with conc H2SO4 then with aqueous NaHCO3 or Na2CO3, and water, followed by drying with CaCl2, K2CO3 or CaSO4, then with P2O5, and distilling. It can also be dried with Linde 4A molecular sieve. Passage through, and storage over, activated alumina has been used to obtain low conductance material. [Flaherty & Stern J Am Chem Soc 80 1034 1958, Beilstein 5 H 199, 5 IV 640.]
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3.5 Shipping
UN1134 Chlorobenzene, Hazard Class: 3;Labels: 3-Flammable liquid.
3.6 Usage
Manufacture of phenol, aniline, DDT; solvent for paint; color printing; dry cleaning industry.
3.7 Waste Disposal
Incineration, preferably aftermixing with another combustible fuel; care must be exercised to assure complete combustion to prevent the formation of phosgene; an acid scrubber is necessary to removethe halo acids produced. Chlorobenzene Preparation Products And Raw materials Preparation Products
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4. Safety and Handling
4.1 Exposure Standards and Regulations
Chlorobenzene is an indirect food additive for use only as a component of adhesives.
4.2 Octanol/Water Partition Coefficient
log Kow = 2.84
4.3 Other Preventative Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Any clothing which becomes /contaminated/ ... with liquid chlorobenzene should be removed immediately and placed in closed containers for storage until it can be discarded, or until provision is made for the removal of the chlorobenzene.
Skin that becomes wet with liquid chlorobenzene should be promptly washed or showered with soap or mild detergent and water to remove any chlorobenzene.
If material /is/ not on fire and not involved in /a/ fire keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.
Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet should be immediately removed due to its flammability hazard (i.e., for liquids with a flash point of
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4.4 Cleanup Methods
Water Spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses.
Air Spill: Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors.
Land Spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply "universal" gelling to immobilize spill. Apply appropriate foam to diminish vapor and fire hazard.
Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use water spray to cool and disperse vapors. Control runoff and isolate discharged material for proper disposal.
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4.5 DisposalMethods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers U037, F002, and D021 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Chlorobenzene is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. Preferably after mixing with another combustible fuel; care must be exercised to assure complete combustion to prevent the formation of phosgene; an acid scrubber is necessary to remove the halo acids produced.
A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids.
A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
Chlorobenzene may be disposed of by atomizing in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. (Afterburner and alkali scrubber). Recommendable method: Incineration.
The thermolysis of Aroclor-1248 was undertaken in a spiralized quartz tubular flow reactor with hydrogen gas inflow at 221 mmol/hr. Temperatures were increased from 715 to 875 deg C over a series of four runs. The duration of each run was 40 to 65 minutes. The product was collected in a trap cooled with liquid nitrogen and analyzed by gas/liquid chromatography. Model runs were also undertaken with chlorobenzene, 1,2,4-trichlorobenzene, and biphenyl at temperatures decreasing over a series of four runs from 875 degrees to 750. Conversions of PCBs were approximately 10, 28, 70, and greater than 99.9% after runs one through four, respectively. Dichlorobenzene and trichlorobenzene accounted for approximately 6% of the Aroclor feed. Chlorobenzene and biphenyl were also products, although the determination of chlorobenzene was obscured by its use as diluent. Methane and small amounts of ethylene, ethane, ethane, and traces of ethyne were also formed. In model runs with chlorobenzene, trichlorobenzene, and biphenyl the amount of biphenyl left was only 0.75%. Dechlorination was again approximately 95%, leaving only traces of 1,2,4-trichlorophenyl. Increasing temperature to 925 degrees increased dechlorination to 99.95%.
The following wastewater treatment technologies have been investigated for chlorobenzene: activated carbon.
The following wastewater treatment technologies have been investigated for chlorobenzene: biological treatment.
The following wastewater treatment technologies have been investigated for chlorobenzene: stripping.
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4.6 DOT Emergency Guidelines
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or regular foam. Large fires: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
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4.7 Fire Fighting Procedures
Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire exposed containers cool.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical or carbon dioxide.
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4.8 FirePotential
Dangerous fire hazard when exposed to heat or flame.
Flammable liquid.
4.9 Safety Profile
Suspected carcinogen. Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. Strong narcotic with slight irritant qualities. Dichlorobenzols are strongly narcotic. Little is known of the effects of repeated exposures at lower concentrations, but it may cause hdney and liver damage. The industrial illnesses reported may possibly be due to nitrobenzol. Dangerous fire hazard when exposed to heat or flame. Moderate explosion hazard when exposed to heat or flame. Potentially explosive reaction with powdered sodium or phosphorus trichloride + sodtum. Violent reaction with AgClO4. Reacts vigorously with oxidizers. See also CHLORINATED HYDROCARBONS, AROMATIC. To fight fire, use foam, CO2, dry chemical, water to blanket fire. Associated with EPA Superfund sites
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4.10 Formulations/Preparations
Grades: Technical
4.11 Incompatibilities
Reacts violently with strong oxidizers;dimethyl sulfoxide; sodium powder; silver perchlorate;causing fire and explosion hazard. Attacks some plastics,rubber, and coatings. Decomposes on heating, producingphosgene and hydrogen chloride fumes.
4.12 Protective Equipment and Clothing
/Wear/ ... neoprene or vinyl gloves; chemical safety spectacles, ... rubber footwear; apron or impervious clothing for splash protection; hard hat.
Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed or when they fail and need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. If the use of respirators is necessary, the only respirators permitted are those that have been approved by the Mine Safety and Health Admin ... or by the National Institute for Occupational Safety and Health.
Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch min), and other appropriate protective clothing necessary to prevent repeated or prolonged skin contact with liquid chlorobenzene. ... Employees should be provided with and required to use splash-proof safety goggles where liquid chlorobenzene may contact the eyes.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Respirator Recommendations: Up to 1000 ppm Assigned Protection Factor (APF) Respirator Recommendation APF = 25 Any supplied-air respirator operated in a continuous-flow mode. Substance causes eye irritation or damage; eye protection needed. APF = 25 Any powered, air-purifying respirator with organic vapor cartridge(s). Substance causes eye irritation or damage; eye protection needed. APF = 50 Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s). APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister. APF = 50 Any self-contained breathing apparatus with a full facepiece. APF = 50 Any supplied-air respirator with a full facepiece.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 10,000 Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. APF = 10,000 Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.
Wear full protective clothing and positive pressure self-contained breathing apparatus.
... Wear appropriate chemical protective gloves, boots and goggles. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material
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4.13 Reactivities and Incompatibilities
Contact with strong oxidizers may cause fires and explosions.
Reacts with strong oxidizing materials.
... Violent reaction with AgClO4.
Strong oxidizers.
Potentially explosive reaction with powdered sodium or phosphorus trichloride + sodium.
Silver perchlorate-acetic acid solvated salt is liable to explode when struck. Shock-sensitive solvated salts are also formed with silver perchlorate and aniline, benzene, chlorobenzene, glycerol, nitrobenzene, pyridine and toluene.
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4.14 Report

NTP Carcinogenesis Studies (gavage); Some Evidence: rat NTPTR* ?? National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-261 ,1985. ; No Evidence: mouse NTPTR* ?? National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-261 ,1985. . Reported in EPA TSCA Inventory. Community Right-To-Know List.

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4.15 Skin, Eye, and Respiratory Irritations
Irritation of the eyes and nose. ...
4.16 Safety

Hazard Codes of Chloro benzene (CAS NO.108-90-7):?HarmfulXn,DangerousN,ToxicT,FlammableF
Risk Statements: 10-20-51/53-40-39-23/24/25-11
R10: Flammable.?
R20: Harmful by inhalation.?
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R40: Limited evidence of a carcinogenic effect.?
R39: Danger of very serious irreversible effects.?
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.?
R11: Highly flammable.
Safety Statements:24/25-61-36/37-45?
S24/25: Avoid contact with skin and eyes.?
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.?
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR:UN 1134 3/PG 3
WGK Germany:2
RTECS:?CZ0175000
F: 3-10
HazardClass: 3
PackingGroup: III
Suspected carcinogen. Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. Strong narcotic with slight irritant qualities. Dichlorobenzols are strongly narcotic. Little is known of the effects of repeated exposures at lower concentrations, but it may cause kidney and liver damage. The industrial illnesses reported may possibly be due to nitrobenzol. Dangerous fire hazard when exposed to heat or flame. Moderate explosion hazard when exposed to heat or flame. Potentially explosive reaction with powdered sodium or phosphorus trichloride + sodium. Violent reaction with AgClO4. Reacts vigorously with oxidizers. See also CHLORINATED HYDROCARBONS, AROMATIC. To fight fire, use foam, CO2, dry chemical, water to blanket fire. Associated with EPA Superfund sites.

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4.17 Specification

First Aid Measures of Chloro benzene (CAS NO.108-90-7):
Eyes:Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:Get medical aid. Wash mouth out with water.
Inhalation:Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Storage of Chloro benzene (CAS NO.108-90-7):
Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Flammables-area.

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4.18 Toxicity
LD50 orally in Rabbit: 2000 - 4000 mg/kg
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Skin irritation, Category 2

Acute toxicity - Inhalation, Category 4

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H226 Flammable liquid and vapour

H315 Causes skin irritation

H332 Harmful if inhaled

H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P233 Keep container tightly closed.

P240 Ground and bond container and receiving equipment.

P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment.

P242 Use non-sparking tools.

P243 Take action to prevent static discharges.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P264 Wash ... thoroughly after handling.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P273 Avoid release to the environment.

Response

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P370+P378 In case of fire: Use ... to extinguish.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P391 Collect spillage.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in CDCl3  
13C NMR : Predict  
1H NMR : 90 MHz in CDCl3  
1H NMR : parameter in CDCl3  
1H NMR : Predict  
Predict 1H proton NMR  
IR : CCl4 solution  
IR : liquid film  
Raman : 4880 A,100M,liquid  
Mass  
Mass spectrum (electron ionization)  
UV/Visible spectrum  
7. Synthesis Route
108-90-7Total: 360 Synthesis Route
 
98-95-3
98-95-3 66 Suppliers
 
108-90-7
108-90-7 93 Suppliers
 
98-88-4
98-88-4 251 Suppliers
 
108-90-7
108-90-7 93 Suppliers
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8. Precursor and Product
precursor:
71-43-2
71-43-2
98-88-4
98-88-4
89-98-5
89-98-5
98-95-3
98-95-3
94-36-0
94-36-0
95-57-8
95-57-8
product:
85-29-0
85-29-0
95-50-1
95-50-1
98-11-3
98-11-3
98-60-2
98-60-2
89-96-3
89-96-3
96-99-1
96-99-1
98-13-5
98-13-5
80-07-9
80-07-9
98-66-8
98-66-8
9. Computed Properties
10.Other Information
Usage
Chlorobenzene is used in organic synthesis and dyestuffs. It is also used as a solvent for adhesives, drugs, rubber, paints and dry cleaning, and as a fiber-swelling agent in textile processing. It is utilized in chemoenzymatic synthesis of (+)-aspicilin and cyclohexane by hydrogenation over colloidal Pt nanocatalysts under ambient conditions.
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Usage
Chlorobenzene is used as a mobile phase in High Performance Liquid Chromatography and Liquid Chromatography coupled with Mass Spectrometry.
Usage
Chlorobenzene is used in spectrophotometry and environmental testing.
Merck
14,2121
BRN
605632
Description
Chlorobenzene is a monocyclic aromatic compound with one hydrogen atom on the benzene ring substituted with one chlorine. It is produced by chlorination of benzene in the liquid phase with a catalyst. Chlorobenzene is a colourless, flammable liquid with a sweet almond-like odor, at ambient temperature with a relatively high vapour pressure, moderate octanol-water partition coefficient (log 2.8) and moderate to low water solubility (497.9 mg/L @ 25℃). Chlorobenzene has a high solubility in nonpolar solvents, however, it is almost insoluble in water. Technical grade Chlorobenzene is typically 99% pure with < 0.05% benzene and < 0.1% dichlorobenzenes as contaminants. It is a common solvent and a widely used intermediate in the manufacture of other chemicals. Rhodococcus phenolicus is a bacterium species able to degrade chlorobenzene as sole carbon sources.
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Uses
  1. Chlorobenzene is used primarily as raw material for the synthesis of o- and p-nitrochlorobenzene and 2,4-dinitrochlorobenzene.Important quantitative chemical conversions other than the production of nitrochlorobenzenes are the production of diphenyl oxide and diphenyldichlorosilane.
  2. Chlorobenzene is mainly used as raw material for the synthesis of chemicals including triphenylphosphine (catalyst for organic synthesis), phenylsilane, and thiophenol (pesticide and pharmaceutical intermediate). It is also used as raw material for the synthesis of solvent for organic synthesis reactions including methylenediphenyldiisocyanate, urethane raw material, agricultural adjuvants, paint and ink, and cleaning solvent for electronics.
  3. manufacture of phenol, aniline, DDT; solvent for paints; heat transfer medium.
  4. Chlorobenzene is used as a process solvent in the production of isocyanates such as MDI and TDI and as a solvent in various crop protection formulations. It is further used as a solvent in condensation reactions in the dyes industry.
  5. Chlorobenzene is a basic substance used in chemical syntheses with 95% of the quantity used converted in closed systems to intermediate and final products.
  6. It is used as a process solvent in the manufacture of three indigoid dyes and pigments. All the pigments and dyes are thioindigoid colors.
  7. Chlorobenzene is an example of haloarenes which is formed by mono substitution of benzene ring. When chlorobenzene is fused with sodium hydroxide at 623K and 320 atm sodium phenoxide is produced. Finally, sodium phenoxide on acidification gives phenols.
    Preparation of phenols from Chlorobenzene
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Toxicity
The toxic effects of chlorobenzene on humans were exhaustion, nausea, lethargy, headache and irritation to the upper respiratory tract and eye. Contact of chlorobenzene with the skin induced irritation. No reports were obtained on sensitization by chlorobenzene in this investigation.
The oral LD50 values of chlorobenzene were 1,445 mg/kg in mice, 1,427 to 3,400 mg/kg in rats and 2,250 to 2,830 mg/kg in rabbits. The LC50s following 6-hr inhalation exposure were 1,889 ppm in mice and 2,968 ppm in rats.
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Description
Chlorobenzene production has been declining since its peak in 1969, and is likely to continue declining due to the substitution of more environmentally friendly chemicals. Chlorobenzene is produced by chlorination of benzene in the presence of a catalyst, and is produced as an end product in the reductive chlorination of di- and trichlorobenzenes. This compound is extensively used in the manufacture of phenol, aniline, and DDT; as a solvent for paints; and as a heat transfer medium. It is also occasionally used in the dry cleaning industry.
Chlorobenzene’s production and use as a chemical intermediate, solvent, and heat transfer medium may result in its release to the environment through various waste streams. If released to air, chlorobenzene will exist solely as a vapor in the atmosphere. Photochemically produced hydroxyl radicals will ultimately degrade vapor-phase chlorobenzene in less than 24 h. Exposure of chlorobenzene to direct sunlight (absorbs at >290 nm) will cause photolysis. Occupational exposure to chlorobenzene may occur through inhalation and dermal contact with this compound at workplaces where chlorobenzene is produced or used. Monitoring data indicate that the general population may be exposed to chlorobenzene via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound.
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Chemical Properties
colourless liquid, Chlorination of benzene in the presence of a catalyst (FeCl3 or AICI3) yields chlorobenzene as the first product. Substitution with a second CI yields ortho, para, or meta dichlorobenzene, Eventually all the hydrogens can be substituted to give hexachlorobenzene, C6C16. In the presence ofultraviolet light, the chlorinationofbenzene yields benzene hexachloride, C6H6C~, a derivative ofcyclohexane.
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Chemical Properties
Chlorobenzene, also called monochlorobenzene, is a monocyclic aromatic compound. It is a colorless liquid with an aromatic almond-like odor and is manufactured for use as a solvent, is used in the production of other chemicals (pesticides), and in making certain other chemicals, rubber, dyes and grease solvents. It is used as a feedstock to produce ortho- and para- nitrochlorobenzenes and aniline; as a solvent for paints; and as a heat transfer medium. In the past,Chlorobenzene was used as an intermediate in phenol and DDT production. Chlorobenzene enters the environment from industrial and municipal discharges. Another potential source is the formation and emission of Chlorobenzene as a product of incomplete combustion in waste incinerators.
Chlorobenzene is moderately soluble in water; up to 1,000 milligrams will mix with a liter of water. Chlorobenzene is slightly persistent in water, with a half-life of between 2 to 20 days. Chlorobenzene persists in soil (several months), in air (3.5 days), and water (less than 1 day).
When heated to decomposition this compound emits toxic fumes of hydrogen chloride gas, CO and CO2. Common synonyms are Monochlorobenzene, Benzene Chloride, and Chlorobenzol. It is incompatible with strong oxidizing agents and dimethyl sulfoxide.
Chlorobenzene (also best known as monochlorobenzene or MCB) is a flammable liquid. Companies also use MCB to make adhesives, paints, paint removers, polishes, dyes, and drugs. In the past companies have used MCB to make phenol and related chemicals, pesticides (like DDT), and aniline.
Chlorobenzene can evaporate when exposed to air. It dissolves slightly when mixed with water. Effects of chlorobenzene on human health and the environment depend on how much chlorobenzene is present and the length and frequency of exposure. Effects also depend on the health of a person or the condition of the environment when exposure occurs.
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Physical properties
Clear, colorless, flammable liquid with a sweet almond, medicinal or mothball-like odor. An odor threshold concentration of 210 ppbv was reported by Leonardos et al. (1969). At 40 °C, the lowest concentration at which an odor was detected was 190 μg/L. At 25 °C, the lowest concentration at which a taste was detected was 190 μg/L (Young et al., 1996). The average least detectable odor threshold concentration in water at 60 °C was 0.08 mg/L (Alexander et al., 1982). Cometto-Mu?iz and Cain (1994) reported an average nasal pungency threshold concentration of 10,553 ppmv.
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Uses
Chlorobenzene is used as a solvent for paints,as a heat transfer medium, and in the manu facture of phenol and aniline.
Uses
Chlorobenzene is a halogenated benzene used in chemical toxicity QSAR research for agricultural pollution.
Uses
Monochlorobenzene is used commercially as a solvent and to produce phenol and nitrochlorobenzenes.
Definition
ChEBI: The simplest member of the class of monochlorobenzenes, that is benzene in which a single hydrogen has been substituted by a chlorine.
Definition
A colorless liquid made by the catalytic reaction of chlorine with benzene. It can be converted to phenol by reaction with sodium hydroxide under extreme conditions (300°C and 200 atmospheres pressure). It is also used in the manufacture of other organic compounds.
Synthesis Reference(s)
Journal of the American Chemical Society, 74, p. 6297, 1952 DOI: 10.1021/ja01144a523
Tetrahedron Letters, 23, p. 371, 1982 DOI: 10.1016/S0040-4039(00)86833-1
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General Description
A colorless to clear, yellowish liquid with a sweet almond-like odor. Flash point 84°F. Practically insoluble in water and somewhat denser than water (9.2 lb / gal). Vapors heavier than air. Used to make pesticides, dyes, and other chemicals.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
Chlorobenzene undergoes a sometimes explosive reaction with powdered sodium or phosphorus trichloride + sodium. May react violently with dimethyl sulfoxide. Reacts vigorously with oxidizing agents. Attacks some forms of plastic, rubber and coatings. Forms a shock sensitive solvated salt with silver perchlorate. .
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Hazard
A possible carcinogen. Avoid inhalation and skin contact. Moderate fire risk. Explosive limits 1.8–9.6%.
Health Hazard
Irritating to skin, eyes and mucous membranes. Repeated exposure of skin may cause dermatitis due to defatting action. Chronic inhalation of vapors or mist may result in damage to lungs, liver, and kidneys. Acute vapor exposures can cause symptoms ranging from coughing to transient anesthesia and central nervous system depression.
Limited information is available on the acute (short-term) effects of chlorobenzene. Acute inhalation exposure of animals to chlorobenzene produced narcosis, restlessness, tremors, and muscle spasms. Chronic (long-term) exposure of humans to chlorobenzene affects the central nervous system (CNS). Signs of neurotoxicity in humans include numbness, cyanosis, hyperesthesia (increased sensation), and muscle spasms. No information is available on the carcinogenic effects of chlorobenzene in humans. EPA has classified chlorobenzene as a Group D, not classifiable as to human carcinogenicity.
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Fire Hazard
Flammable liquid; flash point (closed cup) 29°C (84°F); vapor pressure 8.8 torr at 20°C (68°F); autoignition temperature 638°C (1180°F).
Chlorobenzene vapors form explosive mixtures with air within the range 1.3-7.1% by volume in air. Dimethyl sulfoxide decom poses violently in contact with chloroben zene (NFPA 1997). Many metal perchlorates, such as those of silver and mercury, may form shock-sensitive solvated perchlorates that may explode on impact.
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Safety Profile
Suspected carcinogen. Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. Strong narcotic with slight irritant qualities. Dichlorobenzols are strongly narcotic. Little is known of the effects of repeated exposures at lower concentrations, but it may cause hdney and liver damage. The industrial illnesses reported may possibly be due to nitrobenzol. Dangerous fire hazard when exposed to heat or flame. Moderate explosion hazard when exposed to heat or flame. Potentially explosive reaction with powdered sodium or phosphorus trichloride + sodtum. Violent reaction with AgClO4. Reacts vigorously with oxidizers. See also CHLORINATED HYDROCARBONS, AROMATIC. To fight fire, use foam, CO2, dry chemical, water to blanket fire. Associated with EPA Superfund sites
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Potential Exposure
Chlorobenzene is used in the manufacture of aniline, phenol, and chloronitrobenzene; as an intermediate in the manufacture of dyestuffs and many pesticides, as a solvent; and emulsifier.
Carcinogenicity
Chlorobenzene was not mutagenic in a variety of bacterial and yeast assays. Existing data suggest that genotoxicity may not be an area of concern for chlorobenzene exposure in humans.
Environmental fate
Biological. In activated sludge, 31.5% of the applied chlorobenzene mineralized to carbon dioxide after 5 d (Freitag et al., 1985). A mixed culture of soil bacteria or a Pseudomonas sp. transformed chlorobenzene to chlorophenol (Ballschiter and Scholz, 1980). Pure microbial cultures isolated from soil hydroxylated chlorobenzene to 2- and 4-chlorophenol (Smith and Rosazza, 1974). Chlorobenzene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum. At a concentration of 5 mg/L, biodegradation yields at the end of 1 and 2 wk were 89 and 100%, respectively. At a concentration of 10 mg/L, significant degradation with gradual adaptation was observed.Complete degradation was not observed until after the 3rd week of incubation (Tabak et al.,1981).
https://www.epa.gov
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Shipping
UN1134 Chlorobenzene, Hazard Class: 3; Labels: 3-Flammable liquid.
Purification Methods
The main impurities are likely to be chlorinated impurities originally present in the *benzene used in the synthesis of chlorobenzene, and also unchlorinated hydrocarbons. A common purification procedure is to wash it several times with conc H2SO4 then with aqueous NaHCO3 or Na2CO3, and water, followed by drying with CaCl2, K2CO3 or CaSO4, then with P2O5, and distilling. It can also be dried with Linde 4A molecular sieve. Passage through, and storage over, activated alumina has been used to obtain low conductance material. [Flaherty & Stern J Am Chem Soc 80 1034 1958, Beilstein 5 H 199, 5 IV 640.]
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Toxicity evaluation
In the ambient atmosphere, chlorobenzene will exist as a vapor, and will be degraded by reaction with photochemically produced hydroxyl radicals, with an estimated half-life of 21 days. It can be removed from the air by rain. Photolysis halflives of 4–18 h were measured in aqueous media. If released to soil, chlorobenzene is expected to have very high to moderate mobility based on a Koc range of 4.8–313. Moist soil surfaces will favor volatilization based upon Henry’s Law constant of 3.11×103 atm-cu m mol-1. Chlorobenzene may volatilize from dry soil surfaces as well. If released into water, chlorobenzene may adsorb to suspended solids and sediment based on the Koc values. Volatilization from water surfaces is expected to be an important fate process based on this compound’s Henry’s Law constant. Estimated volatilization half-lives for a model river and model lake are 3.4 h and 4.3 days, respectively. Reported bioconcentration in aquatic organisms is low to high, provided the compound is not metabolized by the organism. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Biodegradation results are variable based on soil type and microbial diversity. In river water, the biodegradation half-life was reported to be 150 and 75 days in the sediment.
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Incompatibilities
Reacts violently with strong oxidizers; dimethyl sulfoxide; sodium powder; silver perchlorate; causing fire and explosion hazard. Attacks some plastics, rubber, and coatings. Decomposes on heating, producing phosgene and hydrogen chloride fumes.
Waste Disposal
Incineration, preferably after mixing with another combustible fuel; care must be exercised to assure complete combustion to prevent the formation of phosgene; an acid scrubber is necessary to remove the halo acids produced.
Storage features
Fireproof. Separated from strong oxidants.
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12. Related Questions
Why is chlorobenzene unreactive?Unreactive towards what? Lithium would react with chlorobenzene, producing phenyllithium. Also, one can perform electrophilic substitution on chlorobenzene, although it is slower to react than benzene..
Why does harsh reaction conditions apply during the formation of phenol from Chlorobenzene?In phenol, due to resonance, the carbon –oxygen bond has a partial double bond character and is difficult to break being stronger than a single bond. Therefore it can not be converted to chlorobenzen..
What happens when chlorobenzene is heated in presence of liAlH4?The reaction is called Nucleophilic Aromatic Substitution, or SNAr for short. Look it up. Your nucleophile is a hydride. Your leaving group will be the chloride anion.
Are phenyl chloride and chlorobenzene the same?Yes. Type chlorobenzene into the PubChem search box and you should see the other name as a synonym in the first result.
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