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Benzoyl chloride

CAS：98-88-4
MW:140.567
MF：C7H5ClO

Benzoyl Chloride is used in the manufacturing of dye intermediates.

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Benzoyl chloride

1.2 Synonyms: 7-Cyanoheptyl benzoate; a-Chlorobenzaldehyde; alpha-Chlorobenzaldehyde; B 0105; Benzaldehyde, α-chloro-; Benzenecarbonyl chloride; Benzoic acid chloride; Benzoic acid, chloride; benzoic chloride; Benzoyl chloride [UN1736] [Corrosive]; BENZOYL CHLORIDE, ACS; Benzoylchloride; BenzoylChlorideGr; Bz chloride; EINECS 202-710-8; MFCD00000653; Phenylcarbonyl chloride; Phenylcarboxyl chloride; α-Chlorobenzaldehyde;

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1.3 CAS No.: 98-88-4

1.4 CID: 7412

1.5 EINECS: 202-710-8

1.6 Molecular Formula: C7H5ClO

1.7 Inchi: InChI=1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H

1.8 InChkey: PASDCCFISLVPSO-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)C(=O)Cl

1.10 Isomers Smiles: C1=CC=C(C=C1)C(=O)Cl

2. Properties

2.1 Vapour pressure: 4.88 (vs air)

2.2 VaporDensity: 4.88 (vs air)

2.3 Appearance: colourless or faintly yellow liquid with a penetrating odour

2.4 Storage: Moisture Sensitive. Ambient temperatures.

2.5 Autoignition Temperature: 197.2 °C

2.6 Color/Form: Transparent, colorless liquid
Slightly brown liquid

2.7 Corrosivity: Slow corrosion of metals

2.8 Decomposition: Hazardous decomposition products formed under fire conditions: Carbon oxides, hydrogen chloride gas.

2.9 Heat of Combustion: -10,030 Btu/lb = -5570 Cal/g = -233.2X10+5 J/kg

2.10 Heat of Vaporization: 11,438.0 gcal/gmol

2.11 Odor: Penetrating odor

2.12 PH: 2 (1g/l, H2O, 20℃)

2.13 Water Solubility: reacts

2.14 Spectral Properties: Index of refraction: 1.5537 @ 20 deg C/D
SADTLER REF NUMBER: 3 (IR, PRISM)
Benzoyl chloride, 99%, exhibits its two strongest infrared absorption bands at wavelengths of 5.6 and 8.3 microns.
IR: 5402 (Sadtler Research Laboratories IR Grating Collection)
UV: 2 (Sadtler Research Laboratories Spectral Collection)
H-1 NMR: 3147 (Sadtler Research Laboratories Spectral Collection)
C-13 NMR: 224 (Johnson and Jankowski, Carbon-13 NMR Spectra, John Wiley and Sons, New York)

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2.15 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, water, alcohols, strong bases.Reacts violently with DMSO and vigorously with alkalies.

2.16 StorageTemp: Store below +30°C.

2.17 Surface Tension: 36.3 dynes/cm = 0.0363 N/m at 20 °C

3. Use and Manufacturing

3.1 Chemical Reactivity: Reactivity with Water Slow reaction with water to produce hydrochloric acid fumes. The reaction is more rapid with steam; Reactivity with Common Materials: Slow corrosion of metals but no immediate danger; Stability During Transport: Not pertinent; Neutralizing Agents for Acids and Caustics: Soda ash and water, lime; Polymerization: Does not occur; Inhibitor of Polymerization: Not pertinent.

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3.2 Definition: A liquid acyl chloride used as a benzoylatingagent.

3.3 Description: Transparent, colorless liquid; pungentodor; vapor causes tears. Soluble in ether and carbon disulfide;decomposes in water. Combustible. Benzoyl chloride is a colorless to slight brownliquid with a strong, penetrating odor.

3.4 Potential Exposure: Benzoyl chloride is used as a chemicalintermediate; in organic synthesis; to produce other chemicals,dyes, perfumes, herbicides, and medicines.

3.5 Purification Methods: A solution of benzoyl chloride (300mL) in *C6H6 (200mL) is washed with two 100mL portions of cold 5% NaHCO3 solution, separated, dried with CaCl2 and distilled [Oakwood & Weisgerber Org Synth III 113 1955]. Repeated fractional distillation at 4mm Hg through a glass helices-packed column (avoiding porous porcelain or silicon-carbide boiling chips, and hydrocarbon or silicon greases on the ground joints) gave benzoyl chloride that did not darken on addition of AlCl3. Further purification is achieved by adding 3 mole% each of AlCl3 and toluene, standing overnight, and distilling off the benzoyl chloride at 1-2mm [Brown & Jenzen J Am Chem Soc 80 2291 1958]. Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used. [Beilstein 9 IV 721.] Strong IRRITANT. Use in a fume cupboard.

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3.6 Usage: Benzoyl Chloride is used in the manufacturing of dye intermediates.

3.7 Waste Disposal: Pour into sodium bicarbonatesolution and flush to sewer. Benzoyl chloride Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 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.
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.
Remove contaminated clothing and shoes. Flush affected areas with plenty of water.
Keep people away. Evacuate area in case of large discharge. Isolate and remove discharged material. Notify local health and pollution control agencies.
If material not on fire and not involved in 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. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. Do not handle broken packages unless wearing protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.

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4.2 Cleanup Methods: Neutralizing agents for acids and caustics: soda ash and water: lime.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, or 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. Apply "universal" gelling agent to immobilize spill.
Environmental considerations: Water spill: If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concentration. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom.
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment.
Stop or control leak, if this can be done without undue risk. Use water spray to cool and protect personnel. Approach release from upwind. Absorb in noncombustible material for proper disposal.
Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer.

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4.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material=s impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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4.4 DOT Emergency Guidelines: /GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Health: CORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns, or death. Fire will produce irritating, corrosive and/or toxic gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control or dilution water may cause pollution.
/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Fire or Explosion: ... Some of these materials may burn, but none ignite readily. May ignite combustibles (wood, paper, oil, clothing, etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases. Flammable/toxic gases may accumulate in confined areas (basement, tanks, hopper/tank cars etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. Substance may be transported in a molten form.
/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75) feet for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Evacuation: ... 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 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Fire: When material is not involved in fire: do not use water on material itself. Small fires: Dry chemical or C02. Move containers from fire area if you can do it without risk. Large Fires: Flood fire area with large quantities of water, while knocking down vapors with water fog. If insufficient water supply: knock down vapors only. Fire involving tanks or car/trailer loads: Cool containers with flooding quantities of water until well after fire is out. Do not get water inside containers. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Spill or Leak: Fully encapsulating, vapor protective clothing should be worn for spills and leaks with no fire. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Use water spray to reduce vapors; do not put water directly on leak, spill area or inside container. Keep combustibles (wood, paper, oil, etc.) away from spilled material. Small spills: Cover with DRY earth, DRY sand, or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. Prevent entry into waterways, sewers, basements or confined areas.
/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. 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. For minor skin contact, avoid spreading material on unaffected skin. Removal of solidified molten material from skin requires medical assistance. Keep victim warm and quiet. 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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4.5 Fire Fighting Procedures: Use foam, carbon dioxide, dry chemical and water fog. /Do not use/ water spray. Do not allow water to enter container.
If material on fire or involved in fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam dry chemical or carbon dioxide.
Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.
Alcohol-resistant foam, powder, carbon dioxide, NO water.

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4.6 FirePotential: Moderate, when exposed to heat or flame.
At fire temperatures the compound may react violently with water or steam.

4.7 Safety Profile: Confirmed carcinogen withexperimental tumorigenic data by skin contact. Humansystemic effects by inhalation: unspecified effects onolfaction and respiratory systems. Corrosive effects on theskin, eyes, and mucous membranes by inhalation.Flammable whe

4.8 Formulations/Preparations: GRADES: Technical; CP
99% +/-; special grade
Benzoyl chloride is available in the US with a minimum of 99.0% active ingredient
Peroxide and agricultural grades

4.9 Incompatibilities: May form explosive mixture with air.Contact with heat, hot surfaces, and flames causes decomposition,forming phosgene and hydrogen chloride. Watercontact may be violent; forms hydrochloric acid. Reactionswith amines, alcohols, alkali metals, dimethyl sulfoxide,strong oxidizers, and metal salts may be violent, causingfire and explosions. Attacks metals in the presence ofmoisture, forming explosive hydrogen gas. Attacks someplastics, rubber or coatings.

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4.10 Protective Equipment and Clothing: Full protective clothing, including full-face respirator for acid gases and organic vapors (yellow gmc canister), close-fitting goggles, non-slip rubber gloves.
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. Self-contained breathing apparatus.
Face shield, or or eye protection in combination with breathing protection. Protective gloves. Protective clothing.

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4.11 Reactivities and Incompatibilities: Dimethyl sulfoxide decomposition is violent on contact with... benzoyl chloride. ...
Mixture of sodium azide and benzoyl chloride reacts spontaneously with evolution of heat in potassium hydroxide solution.
Slow reaction with water to produce hydrochloric acid fumes. Reaction much faster with steam.
Unstabilized benzyl chloride may violently decompose with the rupture of its container in the presence of copper, aluminum, iron, zinc, magnesium, and other catalysts.
Reacts violently with strong oxidants. Reacts with water or steam producing heat, and corrosive fumes (hydrogen chloride). Attacks many metals forming flammable hydrogen gas, also on contact with metal salts. The substance decomposes rapidly on heating or on contact with alkalis, alcohols or amines.

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4.12 Report: Related compounds :BENZOIC ACID, benzoic anhydride, Benzaldehyde

4.13 Skin, Eye, and Respiratory Irritations: Highly irritating to the eye. A potent lacrimator. Vapors highly irritating to the respiratory tract.
Causes severe eye & skin burns. May be harmful if absorbed through skin or inhaled. Irritating to eyes, skin, & respiratory system. Causes severe tearing. May cause pulmonary edema.

4.14 Safety

Hazard Codes?of?Benzoyl chloride (CAS NO.98-88-4):? Corrosive C
Risk Statements: 34?
R34: Causes burns.
Safety Statements: 26-45-36/37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 1736 8/PG 2
WGK Germany:?1
RTECS:?DM6600000
Hazard Note:?Corrosive
HazardClass:?8
PackingGroup:?II
HS Code:?29310095
Hazardous Substances Data: 98-88-4(Hazardous Substances Data)
?

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4.15 Sensitive: Moisture Sensitive

4.16 Specification: Chemical Stability: Air sensitive. Moisture sensitive.?
Conditions to Avoid: Incompatible materials, ignition sources, excess heat, temperatures above 65°C, exposure to moist air or water.?
Incompatibilities with Other Materials Water, strong oxidizing agents, strong bases, alcohols, alkali metals, alkaline earth metals, aluminum, amines, dimethyl sulfoxide, caustics (e.g. ammonia, ammonium hydroxide, calcium hydroxide, potassium hydroxide, sodium hydroxide), explosives (e.g. ammonium nitrate, hydrazoic acid, sodium azide), potassium hydroxide, sodium azide, sulfur oxides.?
Hazardous Decomposition Products Hydrogen chloride, phosgene, carbon monoxide, carbon dioxide.?
Hazardous Polymerization Will not occur.

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4.17 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
human	TCLo	inhalation	2ppm/1M (2ppm)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	"Handbook of Organic Industrial Solvents," 2nd ed., Chicago, National Assoc. of Mutual Casualty Companies, 1961Vol. 2, Pg. 31, 1961.
rat	LC50	inhalation	1870mg/m3/2H (1870mg/m3)	?	"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 25, 1982.
rat	LD50	oral	1900mg/kg (1900mg/kg)	?	Office of Toxic Substances Report. Vol. FYI-OTS-1180-0107,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin corrosion, Category 1B

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H312 Harmful in contact with skin H314 Causes severe skin burns and eye damage H317 May cause an allergic skin reaction H332 Harmful if inhaled
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P333+P313 If skin irritation or rash occurs: Get medical advice/attention.
Storage	P405 Store locked up.
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

IR : CCl4 solution

IR : liquid film

Raman : 4880 A,100M,liquid

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

98-88-4Total: 126 Synthesis Route

65-85-0 917 Suppliers

98-88-4 251 Suppliers

98-07-7 99 Suppliers

98-88-4 251 Suppliers

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8. Precursor and Product

precursor:

98-89-5

93-58-3

79-37-8

93-89-0

94-36-0

65-85-0

93-97-0

85-44-9

98-07-7

product:

92-71-7

98-08-8

55-21-0

98-91-9

85-56-3

93-99-2

94-36-0

93-97-0

94-49-5

98-15-7

9. Computed Properties

Molecular Weight：140.567g/mol
Molecular Formula：C₇H₅ClO
Compound Is Canonicalized：True
XLogP3-AA：140.0028925
Monoisotopic Mass：140.0028925
Complexity：106
Rotatable Bond Count：1
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：1
Topological Polar Surface Area：17.1
Heavy Atom Count：：9
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcYBgIAAEAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgIAAAAADAKAmAAwAIAAAACIAmBaAAACAAAkAAAIiAEAAsgIIDKBFRCAIQAggAAIiYcIiACOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: Benzoyl chloride is widely utilized for the synthesis of peroxides. It is employed in the production of dyes and perfumes. It also serves in the manufacturing of pharmaceuticals and resins.

Merck: 14,1112

BRN: 471389

Physical and Chemical Properties: Its pure product is a colorless and transparent flammable liquid, which is smoking exposed to air in the air. In Industry, it is slightly pale yellow, with a strong pungent odor. Its steam has a strong stimulating effect for eye mucous membranes, skin and respiratory tract, by stimulating the mucous membranes and eyes tear. Benzoyl chloride Melting point is-1.0 ℃, boiling point is 197.2 ℃, and the relative density is 1.212 (20 ℃), while a flash point is 72 ℃, and refractive index (n20) is 1.554. It is soluble in the ether, chloroform, benzene and carbon disulfide. It can gradually decomposed in water or ethanol, ammonia, which generates benzoic acid, generating benzamide, ethyl benzoate and hydrogen chloride. In the laboratory, it can be obtained by distillation of benzoic acid and phosphorus pentachloride under anhydrous conditions. Industrial production process can be obtained by the use of thionyl chloride benzaldehyde. Benzoyl chloride is an important intermediate for preparing dyes, perfumes, organic peroxides, resins and drugs. It is also used in photography and artificial tannin production, which was formerly used as an irritant gas in chemical warfare.

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Application: Benzoyl chloride is used for organic synthesis, dye and pharmaceutical raw material, manufacturing initiator benzoyl peroxide, t-butyl peroxybenzoate, pesticides and herbicides. In pesticides, it is a new insecticide, which is inducible isoxazole parathion (Isoxathion, Karphos) intermediate. Benzoyl chloride is an important benzoyl and benzyl reagent. Most of benzoyl chloride is used in the production of benzoyl peroxide, and secondly for the production of benzophenone, benzyl benzoate, benzyl cellulose. Benzoyl peroxide catalyzes polymerization initiator for the monomer plastic, polyester, epoxy, acrylic resin production, self-curing agent, which is a glass fiber material, fluorine rubber, silicone crosslinking agents, oil refined, bleached flour, fiber decolorizing.

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Chemical Properties: Transparent, colorless liquid; pungent odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible.

Chemical Properties: Benzoyl chloride is a colorless to slight brown liquid with a strong, penetrating odor.

Uses: Benzoyl Chloride is used in the manufacturing of dye intermediates.

Uses: For acylation, i.e., introduction of the benzoyl group into alcohols, phenols, and amines (Schotten-Baumann reaction); in the manufacture of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivatives for identification purposes.

Definition: A liquid acyl chloride used as a benzoylating agent.

Production Methods: Benzoyl chloride can be prepared from benzoic acid by reaction with PCl5 or SOCl2, from benzaldehyde by treatment with POCl3 or SO2 Cl2, from benzotrichloride by partial hydrolysis in the presence of H2SO4 or FeCl3, from benzal chloride by treatment with oxygen in a radical source, and from several other miscellaneous reactions. Benzoyl chloride can be reduced to benzaldehyde, oxidized to benzoyl peroxide, chlorinated to chlorobenzoyl chloride and sulfonated to m-sulfobenzoic acid. It will undergo various reactions with organic reagents. For example, it will add across an unsaturated (alkene or alkyne) bond in the presence of a catalyst to give the phenylchloroketone:

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Synthesis Reference(s): Journal of the American Chemical Society, 73, p. 702, 1951 DOI: 10.1021/ja01146a061
Synthesis, p. 306, 1983 DOI: 10.1055/s-1983-30314

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General Description: A colorless fuming liquid with a pungent odor. Flash point 162°F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals.

Reactivity Profile: Benzoyl chloride reacts violently with protic solvents such as alcohols, with amines and amides (for example dimethylformamide [Bretherick 1979 p. 6] ) and with inorganic bases. Causes the violent decomposition of dimethyl sulfoxide [Chem. Eng. News 35(9): 87 1957]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Friedel-Crafts acylation of naphthalene using Benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].

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Hazard: Highly toxic. Strong irritant to skin, eyes, and mucous membranes, and via ingestion, inhala- tion. Upper respiratory tract irritant. Probable car- cinogen.

Health Hazard: INHALATION: may irritate eyes, nose and throat. INGESTION: causes acute discomfort. SKIN: causes irritation and burning.

Chemical Reactivity: Reactivity with Water Slow reaction with water to produce hydrochloric acid fumes. The reaction is more rapid with steam; Reactivity with Common Materials: Slow corrosion of metals but no immediate danger; Stability During Transport: Not pertinent; Neutralizing Agents for Acids and Caustics: Soda ash and water, lime; Polymerization: Does not occur; Inhibitor of Polymerization: Not pertinent.

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Safety Profile: Confirmed carcinogen withexperimental tumorigenic data by skin contact. Humansystemic effects by inhalation: unspecified effects onolfaction and respiratory systems. Corrosive effects on theskin, eyes, and mucous membranes by inhalation.Flammable whe

Potential Exposure: Benzoyl chloride is used as a chemical intermediate; in organic synthesis; to produce other chemicals, dyes, perfumes, herbicides, and medicines.

Shipping: UN 1736 Benzoylchloride, Hazard class: 8; Labels: 8—Corrosive material.

Purification Methods: A solution of benzoyl chloride (300mL) in *C6H6 (200mL) is washed with two 100mL portions of cold 5% NaHCO3 solution, separated, dried with CaCl2 and distilled [Oakwood & Weisgerber Org Synth III 113 1955]. Repeated fractional distillation at 4mm Hg through a glass helices-packed column (avoiding porous porcelain or silicon-carbide boiling chips, and hydrocarbon or silicon greases on the ground joints) gave benzoyl chloride that did not darken on addition of AlCl3. Further purification is achieved by adding 3 mole% each of AlCl3 and toluene, standing overnight, and distilling off the benzoyl chloride at 1-2mm [Brown & Jenzen J Am Chem Soc 80 2291 1958]. Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used. [Beilstein 9 IV 721.] Strong IRRITANT. Use in a fume cupboard.

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Incompatibilities: May form explosive mixture with air. Contact with heat, hot surfaces, and flames causes decomposition, forming phosgene and hydrogen chloride. Water contact may be violent; forms hydrochloric acid. Reactions with amines, alcohols, alkali metals, dimethyl sulfoxide, strong oxidizers, and metal salts may be violent, causing fire and explosions. Attacks metals in the presence of moisture, forming explosive hydrogen gas. Attacks some plastics, rubber or coatings.

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Waste Disposal: Pour into sodium bicarbonate solution and flush to sewer.

11. Toltal 225 Suppliers View more

Benzoyl Chloride,Benzenecarbonyl chloride,98-88-4

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12. Related Questions

: How is Benzaldehyde Formed from Benzoyl Chloride?Benzoyl chloride undergoes a transformation into benzaldehyde through the Rosenmund reaction. This reaction involves the hydrogenation of chloride using a catalyst (palladium on barium sulphate) to pr..; Can Benzoyl Chloride Be a Potential Alternative for Other Drug Release Systems?Are you curious about the potential of Benzoyl chloride to serve as an alternative to other drug release systems? This article will explore the application of Benzoyl chloride in the pharmaceutical fi..; What is Benzoyl Chloride and its Applications?What is Benzoyl Chloride? Benzoyl chloride is a type of acyl chloride that is commonly used in various industries. It is a colorless, transparent, and flammable liquid that emits smoke when exposed to..; What are the properties, uses, and hazards of Benzoyl chloride?Benzoyl chloride (CAS: 98-88-4), also known as phenyl chloride, is a colorless fuming liquid with an irritating odor. In the laboratory, it can be obtained by distilling benzoic acid and phosphorus pe..

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