Encyclopedia / Agrochemicals & Pesticides / Pharmaceutical Intermediates / Organic Intermediate

1,4-Dichlorobenzene

CAS：106-46-7
MW:147.00196
MF：C6H4Cl2

A white colored liquid with the odor of moth balls. Denser than water and insoluble in water. Flash point below 200°F. Used as a moth repellent, to make other chemicals, as a fumigant, and for many other uses. View more+

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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: 1,4-Dichlorobenzene

1.2 Synonyms: 1,5-Dichlorobenzene; 2,5-dichlorobenzene; 4-chlorophenyl chloride; Benzene, 1,4-dichloro-; Benzene, p-dichloro-; Benzene,1,4-dichloro-,compd.withtetrakis(4-methylpyridine)bis(thiocyanato-N)iron(1:1); Benzene,p-dichloro-; caswellno632; Dichlorobenzene; dichlorobenzene(non-specificname); Dichlorobenzene, 1,4-; Dichlorobenzene, p-; Dichlorobenzene, para; dichlorobenzene,para,solid; EINECS 203-400-5; MFCD00000604; Paracide; paradichlorobenzene; para-Dichlorobenzene; pdb; p-Dichlorbenzene; p-dichlorobenzene;

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1.3 CAS No.: 106-46-7

1.4 CID: 4685

1.5 EINECS: 203-400-5

1.6 Molecular Formula: C6H4Cl2

1.7 Inchi: InChI=1S/C6H4Cl2/c7-5-1-2-6(8)4-3-5/h1-4H

1.8 InChkey: OCJBOOLMMGQPQU-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1Cl)Cl

1.10 Isomers Smiles: C1=CC(=CC=C1Cl)Cl

2. Properties

2.1 Vapour pressure: 5.07 (vs air)

2.2 Solubility: 0.08g/l

2.3 Viscosity: 0.839 mPa.s at 55 °C; 0.668 mPa.s at 79 °C

2.4 VaporDensity: 5.07 (vs air)

2.5 Appearance: white crystal flakes

2.6 Atmospheric OH Rate Constant: 3.20e-13 cm3/molecule*sec

2.7 Storage: Ambient temperatures.

2.8 Autoignition Temperature: No autoflammability up to 500 °C.

2.9 Carcinogenicity: 1,4-Dichlorobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

2.10 Chemical Properties: colourless or white crystals

2.11 Color/Form: White crystals
Colorless or white crystalline solid ...

2.12 Corrosivity: Non-corrosive

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

2.14 Heat of Vaporization: 49.0 kJ/mol at 25 °C

2.15 HenrysLawConstant: 0.00 atm-m3/mole

2.16 Ionization Potential: 8.98 eV

2.17 Odor: Distinctive aromatic odor ... becomes very strong at concentrations between 30 and 60 ppm

2.18 PH: 7 (0.06g/l, H2O, 20℃)

2.19 Water Solubility: insoluble

2.20 Spectral Properties: Intense mass spectral peaks: 146 m/z (100%), 148 m/z (64%), 111 m/z (35%), 75 m/z (22%)
IR: 4279 (Coblentz Society Spectral Collection)
UV: 55 (Sadtler Research Laboratories Spectral Collection)
NMR: 715 (Sadtler Research Laboratories Spectral Collection)
MASS: 818 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

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2.21 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, aluminium and its alloys, some plastics.

2.22 StorageTemp: 2-8°C

2.23 Surface Tension: 31.4 dynes/cm

3. Use and Manufacturing

3.1 Agricultural Uses: Insecticide, Rodenticide, Fungicide: p-Dichlorbenzene is used primarily as an air deodorant,as moth balls, and in insecticides, which accounts for90% of the total production of this isomer. Information isnot available concerning the production and use of m-DCB.However, it may occur as a contaminant of o-or p-DCBformulations. Both o-and p-isomers are produced almostentirely as byproducts during the production of monochlorobenzene.The major uses of o-DCB are as a process solventin the manufacturing of toluene diisocyanate and asan intermediate in the synthesis of dyestuffs, herbicides,and degreasers. The para-isomer of dichlorobenzene is theisomer most prominently used in agriculture. Not listed foruse in EU countries.

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3.2 Chemical Reactivity: Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

3.3 Definition: ChEBI: A dichlorobenzene carrying chloro groups at positions 1 and 4.

3.4 Description: colourless or white crystals There are three isomeric forms of dichlorobenzene (DCB):m-DCB is a flammable liquid and vapor.ChEBI: A dichlorobenzene carrying chloro groups at positions 1 and 4. dichlorobenzene: Any one of threeisomeric liquid aromatic compounds,C6H4Cl2. 1,2-Dichlorobenzene (b.p.179°C) and 1,4-dichlorobenzene (b.p.174°C) are made by chlorinatingbenzene with an iron catalyst andseparating the mixed isomers byfractional distillation; 1,3-dichlorobenzene(b.p. 172°C) is made fromon

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3.5 Potential Exposure: The major uses of o-DCB are asa process solvent in the manufacturing of toluene diisocyanate and as an intermediate in the synthesis of dyestuffs,herbicides, and degreasers. p-Dichlorbenzene is usedprimarily as a moth repellant, a mildew control agent;space deodorant; and in insecticides, which accounts for90% of the total production of this isomer. Information isnot available concerning the production and use of m-DCB.However, it may occur as a contaminant of o-or p-DCBformulations. Both o-and p-isomers are produced almostentirely as by-products during the production ofmonochlorobenzene

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3.6 Purification Methods: o-Dichlorobenzene is a common impurity. The p-isomer has been purified by steam distillation, crystallisation from EtOH or boiling MeOH, air-dried and dried in the dark under vacuum. It has also been purified by zone refining. [Beilstein 5 IV 658.]

3.7 Shipping: m-DCB: UN2810 Toxic liquids, organic, n.o.s.,Hazard Class: 6.1; Labels: 6.1-Poisonous materials,Technical Name Required. United States DOT RegulatedMarine Pollutant. UN3077 Environmentally hazardoussubstances, solis, n.o.s., Hazard class: 9; Labels:9-Miscellaneous hazardous material, Technical NameRequired. UN3082 Environmentally hazardous substances,liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

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3.8 Usage: The compound 1,4-dichlorobenzene is most commonly referred to as para-DCB or p-DCB. It is widely used as a moth killer, in space deodorizers, and in the production of polyphenylene sulfide. It is also used in the manufacture of certain resins, in the pharmaceutical industry, and as a general insecticide in farming. At room temperature, 1,4- dichlorobenzene is a white or colorless crystalline solid with a characteristic penetrating odor. When exposed to air, it is slowly transformed from its solid state into a vapor; the released vapor then acts as a deodorizer and insect killer. It is practically insoluble in water and is soluble in alcohol, acetone, ether, chloroform, carbon disulfide, and benzene. Its chemical formula is C6H4Cl2. There is limited evidence that 1,4-dichlorobenzene can damage a developing fetus. Exposure can damage the lungs, liver, kidneys, and blood cells, causing anemia; it can also cause swelling of the eyes, hands, and feet. It can damage the nervous system, causing weakness, trembling, and numbness in the arms and legs. It may cause a skin allergy, which when developed can cause itching and a skin rash. Higher levels of the chemical in air, such as the levels that are sometimes associated with industrial exposure, can cause headaches, nausea, clumsiness, slurred speech, and dizziness. Levels that would result in death would be associated with an odor so intense that it would be very unpleasant, if not intolerable, and would serve as a danger warning. In industrial situations, workers exposed to 1,4- dichlorobenzene at high levels are usually directed to wear respirators. Workers involved in the production of the chemical may be exposed to concentrations significantly higher than those encountered by the general population. High exposure levels may result from some consumer products of moth repellents and room deodorizers. Approximately 95% of the environmental release of 1,4- dichlorobenzene occurs during its use, rather than during its manufacture or processing.

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4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow = 3.44

4.2 Fire Hazard: Special Hazards of Combustion Products: Vapors are irritating. Toxic chlorine, hydrogen chloride, and phosgene gases may be generated in fires.

4.3 Other Preventative Measures: Do not get in eyes or on clothing. Avoid contact with skin. Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash before reused. /99.9% Paradichlorobenzene/
Harmful if swallowed or absorbed through skin. Causes eye, skin, and respiratory tract irritation. Wear goggles or face shield. Do not get in eyes or on clothing. Avoid contact with skin. Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash before reuse. /99.9% Paradichlorobenzene/
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: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
The worker should immediately wash the skin when it becomes contaminated.
The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the body with copious amounts of water or soap and water..
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself and any of your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
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.

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4.4 Cleanup Methods: ENVIRONMENTAL HAZARDS: Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance contact your State Water Board or Regional Office of the EPA.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./
Environmental considerations: 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. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.
After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

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4.5 DisposalMethods: Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U072 & D027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
p-Dichlorobenzene may be disposed of: 1) by making packages of p-dichlorobenzene in paper or other flammable material and burning in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. 2) By dissolving p-dichlorobenzene in a flammable solvent (such as alcohol) and atomizing in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. Recommendable method: Incineration.
... Halogenated compounds may be disposed of by incineration provided they are blended with other compatible wastes or fuels so that the composite contains less than 30% halogens and the heating value is from 7000 to 9000 BTU/lb. Liquid injection, rotary kiln, and fluidized bed incinerators are typically used to destroy liquid halogenated wastes. ... Temperatures of at least 2000 - 2200 deg F and residence times /of more than 2 sec/ ... are required for the destruction of halogenated aromatic hydrocarbons.
EPA 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.
Chemical Treatability of 1,4-Dichlorobenzene; Concentration Process: Stripping; Chemical Classification: Aromatic; Scale of Study: Full Scale, Continuous Flow; Type of Wastewater Used: Domestic Wastewater; Results of Study: 90% reduction by air stripping.
Chemical Treatability of 1,4-Dichlorobenzene; Concentration Process: Activated Carbon; Chemical Classification: Aromatic; Scale of Study: Full scale, Continuous Flow; Type of Wastewater Used: Domestic Wastewater; Results of Study: 60% removal; (treatment of effluent from 0.66 cu m/sec biological system).
Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) perimit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to the sewer systems without previously notifing the local sewage treatment plant authority.
Pesticide Disposal: Waste resulting from the use of this product must be disposed of at an approved waste disposal facility.
Container Disposal: Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or by other procedures approved by state and local authorities. Reuse is limited to the same class of pesticide or to non-pesticide products, provided reuse is in compliance with all regulations. This label must be removed prior to any container reuse.
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

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4.6 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. Extinguish fire using agent suitable for surrounding fire. /o-Dichlorobenzene/
Water may be used to blanket fire.
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.).

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4.7 Safety Profile: Confirmed carcinogen with experimental carcinogenic data. An experimental teratogen. A human poison by an unspecified route. Moderately toxic to humans by ingestion. Moderately toxic experimentally by ingestion, subcutaneous, and intraperitoneal routes. Other experimental reproductive effects. Human systemic effects by ingestion: unspecified changes in the eyes, lungs, thorax and respiration, and decreased motihty or constipation. Can cause liver injury in humans. A human eye irritant. Mutation data reported. A fumigant. Flammable liquid when exposed to heat, flame, or oxidizers. Dangerous; can react vigorously with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC.

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4.8 Formulations/Preparations: COMMERCIAL PARA-DICHLOROBENZENE IS AVAIL IN USA AS TECHNICAL GRADE LIQUID
Crystalline material pressed into various forms; solutions in volatile solvents or in an oil suspension.
Technical grade with high purity: 100% in crystalline form and 99.92% in liquid form (on an anhydrous basis)
IT IS ALSO AVAIL AS CRYSTALS IN SEVERAL PARTICLE SIZES CONTAINING NO DETECTABLE IMPURITIES.
Pure-grade para-dichlorobenzene consists of >99.8% para-dichlorobenzene,
Formulation Types: Cakes, crystals, balls, sachetes, impregnated strips, blocks, varpel rope, and flakes.
Para-Dichlorobenzene: Active Ingredient 99.9 % Paradichlorobenzene.
ENOZ MOTH ICE CRYSTALS: Active Ingredient 99.9 % Paradichlorobenzene.
ENOZ MOTH CAKE: Active Ingredient 99.9 % Paradichlorobenzene.
PARADICHLOROBENZENE: Active Ingredient 99.9 % Paradichlorobenzene.
ENOZ PARA MOTH BALLS: Active Ingredient 99.9 % Paradichlorobenzene.
ENOZ NO CLINGING ODOR MOTH CAKE: Active Ingredient 99.9 % Paradichlorobenzene.
ENOZ MOTH BAR: Active Ingredient 99.72 % Paradichlorobenzene.
MOTH-TEK PAPER COVERED MOTH BALL PACKETS: Active Ingredient 99.68 % Paradichlorobenzene.
REEFER-GALLER OLD FASHIONED LAVENDER SCENTED MOTH SACHETTE: Active Ingredient 99.59 % Paradichlorobenzene.
REEFER-GALLER NO-MOTH CAKES: Active Ingredient 99.9 % Paradichlorobenzene.
8 IN 1 BIRD PROTECTOR: Active Ingredient 50 % Paradichlorobenzene.
DOUBLE DUTY BIRD GUARD: Active Ingredient 50 % Paradichlorobenzene.
PERFUMED MOTH BLOCK: Active Ingredient 99.7 % Paradichlorobenzene.
AUSTIN'S MOTH CONTROL: Active Ingredient 99.9 % Paradichlorobenzene.
FEATHER GLO BIRD-CAGE-DEFENDER: Active Ingredient 50 % Paradichlorobenzene.
VARPEL ROPE: Active Ingredient 98.6 % Paradichlorobenzene.
PARA-MOTH: Active Ingredient 100 % Paradichlorobenzene.
PARA MOTHBALLS: Active Ingredient 99.5 % Paradichlorobenzene.
SANTOCHLOR MOLTEN INSECTICIDE: Active Ingredient 99.94 % Paradichlorobenzene.
SANTOCHLOR FLAKES: Active Ingredient 99.94 % Paradichlorobenzene.
PARADICHLOROBENZENE: Active Ingredient 99.8 % Paradichlorobenzene.
IMS MOTH BALLS: Active Ingredient 99.8 % Paradichlorobenzene.
IMS MOTH BLOCK: Active Ingredient 99.6 % Paradichlorobenzene.
IMS MOTH CAKE: Active Ingredient 99.8 % Paradichlorobenzene.
IMS MOTH CRYSTALS: Active Ingredient 99.8 % Paradichlorobenzene.
MOTH-BE-GONE MOTH BALLS 1: Active Ingredient 99.72 % Paradichlorobenzene.
MOTH AVOID MOSTURE ABSORBING MOTH BALL SACHET: Active Ingredient 65 % Paradichlorobenzene.

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4.9 Incompatibilities: For o-DCB and m-DCB: acid fumes,chlorides, strong oxidizers; hot aluminum, or aluminumalloys. For p-DCB: Strong oxidizers; although, incompatibilities for this chemical may also include other materialslisted for o-DCB.

4.10 Protective Equipment and Clothing: Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles.
Respirator Recommendations: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration: 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.

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4.11 Reactivities and Incompatibilities: Dangerous: when heated to decomposition or on contact with acids or acid fumes they evolve highly toxic /hydrogen chloride/ fumes. Can react vigorously with oxidizing materials.
Strong oxidizers (such as chlorine or permanganate).

4.12 Skin, Eye, and Respiratory Irritations: Exposure to p-dichlorobenzene may cause irritation of the eyes, nose, and throat.
Vapors & sprays are irritating to eyes, nose & throat.
It causes substantial but temporary eye injury. /99.9% Paradichlorobenzene/

4.13 Safety: Hazard Codes:Xn,N,T,F
Risk Statements:36-40-50/53-39/23/24/25-23/24/25-11
36:Irritating to the eyes
40:Limited evidence of a carcinogenic effect
50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
11:Highly Flammable
Safety Statements:36/37-46-60-61-45-16-7
36/37:Wear suitable protective clothing and gloves
46:If swallowed, seek medical advice immediately and show this container or label
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
16:Keep away from sources of ignition - No smoking
7:Keep container tightly closed
RIDADR:UN 3077 9/PG 3
WGK Germany:2
HazardClass:9
PackingGroup:III
HS Code:29036100
Hazardous Substances Data:106-46-7(Hazardous Substances Data)

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4.14 Specification: colourless or white crystals
Safety Statements:36/37-46-60-61-45-16-7
36/37:Wear suitable protective clothing and gloves
46:If swallowed, seek medical advice immediately and show this container or label
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
16:Keep away from sources of ignition - No smoking
7:Keep container tightly closed

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4.15 Toxicity: INHALATION: irritation of upper respiratory tract; over- exposure may cause depression and injury to liver and kidney. EYE CONTACT: pain and mild irritation.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

Carcinogenicity, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H319 Causes serious eye irritation H351 Suspected of causing cancer H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P273 Avoid release to the environment.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P308+P313 IF exposed or concerned: Get medical advice/ attention. P391 Collect spillage.
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

1H NMR : parameter in CDCl3

1H NMR : parameter in cyclohexane

1H NMR : parameter neat

IR : CCl4 solution

IR : KBr disc

Raman : 4880 A,100M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

106-46-7Total: 169 Synthesis Route

98-60-2 143 Suppliers

106-46-7 278 Suppliers

71-43-2 202 Suppliers

106-46-7 278 Suppliers

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8. Precursor and Product

precursor:

71-43-2

98-60-2

95-94-3

98-67-9

80-07-9

95-82-9

98-66-8

product:

120-82-1

97-50-7

88-87-9

88-42-6

95-94-3

95-95-4

108-90-7

95-82-9

9. Computed Properties

Molecular Weight：147.00196g/mol
Molecular Formula：C₆H₄Cl₂
Compound Is Canonicalized：True
XLogP3-AA：145.9690055
Monoisotopic Mass：145.9690055
Complexity：54.9
Rotatable Bond Count：0
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：0
Topological Polar Surface Area：0
Heavy Atom Count：：8
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：AAADcYBgAAAGAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGAIAAAAACAKAECAwAIAAAACAACBCAAACAAAgBQAIiAAAAogIICKBExCAIAAggAAIiAcAAAAAAAAQAAAAAAAAACAAAAAAAAAAAAAAAA==

10.Other Information

Usage: 1,4-Dichlorobenzene, is used as moth repellant, air fresheners and toilet blocks and general deodorant for garbage and restrom as well as to control fruit borers and ants, may be applied to tobacco seed beds for blue mold control. It is also used as a pharmaceutical intermediate. 1,4-dichlorobenzene is as a used as a minor processing aid in the production of grinding wheels.

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Merck: 14,3057

BRN: 1680023

Description: Paradichlorobenzene, or PDB, also commonly known as mothballs, are white, volatile crystals with a penetrating odor. Boiling point is 345°F (173°C), flash point is 150°F (65.6°C), and the melting point is 127°F (52°C). PDB is insoluble in water and has a specific gravity of 1.5, which is heavier than water. Vapor density is 5.1, which is heavier than air. In addition to being flammable, it is also toxic by ingestion and an irritant to the eyes, with a TLV of 75 ppm in air. The four-digit UN identification number is 1592. The NFPA 704 designation for PDB is health 2, flammability 2, and reactivity 0. The primary uses are as a moth repellent, a general insecticide, a soil fumigant, and in dyes.

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Chemical Properties: colourless or white crystals

Chemical Properties: There are three isomeric forms of dichlorobenzene (DCB): m-DCB is a flammable liquid and vapor.

Physical properties: Colorless to white crystals with a penetrating, sweet, mothball or almond-like odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 18 and 4.5 μg/L, respectively. Similarly, at 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 32 and 11 μg/L, respectively (Young et al., 1996). A detection odor threshold concentration of 73 μg/m³ (121 ppb_v) was reported by Punter (1983).

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Uses: The compound 1,4-dichlorobenzene is most commonly referred to as para-DCB or p-DCB. It is widely used as a moth killer, in space deodorizers, and in the production of polyphenylene sulfide. It is also used in the manufacture of certain resins, in the pharmaceutical industry, and as a general insecticide in farming. At room temperature, 1,4- dichlorobenzene is a white or colorless crystalline solid with a characteristic penetrating odor. When exposed to air, it is slowly transformed from its solid state into a vapor; the released vapor then acts as a deodorizer and insect killer. It is practically insoluble in water and is soluble in alcohol, acetone, ether, chloroform, carbon disulfide, and benzene. Its chemical formula is C₆H₄Cl₂.
There is limited evidence that 1,4-dichlorobenzene can damage a developing fetus. Exposure can damage the lungs, liver, kidneys, and blood cells, causing anemia; it can also cause swelling of the eyes, hands, and feet. It can damage the nervous system, causing weakness, trembling, and numbness in the arms and legs. It may cause a skin allergy, which when developed can cause itching and a skin rash. Higher levels of the chemical in air, such as the levels that are sometimes associated with industrial exposure, can cause headaches, nausea, clumsiness, slurred speech, and dizziness. Levels that would result in death would be associated with an odor so intense that it would be very unpleasant, if not intolerable, and would serve as a danger warning. In industrial situations, workers exposed to 1,4- dichlorobenzene at high levels are usually directed to wear respirators. Workers involved in the production of the chemical may be exposed to concentrations significantly higher than those encountered by the general population. High exposure levels may result from some consumer products of moth repellents and room deodorizers. Approximately 95% of the environmental release of 1,4- dichlorobenzene occurs during its use, rather than during its manufacture or processing.

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Uses: 1,4-Dichlorobenzene is used as a fumigantand as an insecticide.

Uses: Insecticidal fumigant. For domestic use against clothes moths; as space deodorant in room deodorizers, toilet bowl blocks and diaper pail deodorizers. Intermediate in production of plastics for electronic components.

Definition: ChEBI: A dichlorobenzene carrying chloro groups at positions 1 and 4.

Definition: dichlorobenzene: Any one of threeisomeric liquid aromatic compounds,C6H4Cl2. 1,2-Dichlorobenzene (b.p.179°C) and 1,4-dichlorobenzene (b.p.174°C) are made by chlorinatingbenzene with an iron catalyst andseparating the mixed isomers byfractional distillation; 1,3-dichlorobenzene(b.p. 172°C) is made fromone of the other two by catalytic isomerization.The 1,2 isomer is used asan insecticide and in making dyes;the 1,4 compound is employed as adeodorant and moth repellent.

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Synthesis Reference(s): Chemistry Letters, 8, p. 939, 1979
The Journal of Organic Chemistry, 48, p. 250, 1983 DOI: 10.1021/jo00150a020
Tetrahedron Letters, 23, p. 371, 1982 DOI: 10.1016/S0040-4039(00)86833-1

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General Description: A white colored liquid with the odor of moth balls. Denser than water and insoluble in water. Flash point below 200°F. Used as a moth repellent, to make other chemicals, as a fumigant, and for many other uses.

Air & Water Reactions: Insoluble in water.

Reactivity Profile: 1,4-Dichlorobenzene is incompatible with oxidizing agents. 1,4-Dichlorobenzene is also incompatible with aluminum and its alloys. 1,4-Dichlorobenzene liquefies when mixed with camphor, phenol and salol. 1,4-Dichlorobenzene will attack some forms of plastics, rubber and coatings. .

Health Hazard: INHALATION: irritation of upper respiratory tract; over- exposure may cause depression and injury to liver and kidney. EYE CONTACT: pain and mild irritation.

Health Hazard: Toxic symptoms are headache, weakness,dizziness, nausea, vomiting, diarrhea, loss ofweight, and injury to liver and kidney. Thesesymptoms occur from repeated inhalationof high concentrations of vapors or fromingestion. The vapors are an irritant to theeyes, throat, and skin. Chronic exposure maycause jaundice and cirrhosis. The oral LD50value in mice is in the range 3000 mg/kg.The fatal oral dose in humans is estimated tobe 40–50 g. Carcinogenic studies on animalshave not produced adequate evidence of anycancer-causing action.

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Fire Hazard: Special Hazards of Combustion Products: Vapors are irritating. Toxic chlorine, hydrogen chloride, and phosgene gases may be generated in fires.

Chemical Reactivity: Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Agricultural Uses: Insecticide, Rodenticide, Fungicide: p-Dichlorbenzene is used primarily as an air deodorant, as moth balls, and in insecticides, which accounts for 90% of the total production of this isomer. Information is not available concerning the production and use of m-DCB. However, it may occur as a contaminant of o-or p-DCB formulations. Both o-and p-isomers are produced almost entirely as byproducts during the production of monochlorobenzene. The major uses of o-DCB are as a process solvent in the manufacturing of toluene diisocyanate and as an intermediate in the synthesis of dyestuffs, herbicides, and degreasers. The para-isomer of dichlorobenzene is the isomer most prominently used in agriculture. Not listed for use in EU countries.

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Trade name: DowTHERM?; EVOLA; PARACIDE?; PARA CRYSTALS?; PARADI?; PARADOW?; PARAMOTH?; PARANUGGETS?; PARAZENE?; PERSIA-PERAZOL?; SANTOCHLOR?; Mixed isomers: DILATIN DBI?; MOTTENSCHUTZMITTEL EVAU P?; MOTT-EX?; TOTAMOTT?

Safety Profile: Confirmed carcinogen with experimental carcinogenic data. An experimental teratogen. A human poison by an unspecified route. Moderately toxic to humans by ingestion. Moderately toxic experimentally by ingestion, subcutaneous, and intraperitoneal routes. Other experimental reproductive effects. Human systemic effects by ingestion: unspecified changes in the eyes, lungs, thorax and respiration, and decreased motihty or constipation. Can cause liver injury in humans. A human eye irritant. Mutation data reported. A fumigant. Flammable liquid when exposed to heat, flame, or oxidizers. Dangerous; can react vigorously with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC.

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Potential Exposure: The major uses of o-DCB are as a process solvent in the manufacturing of toluene diisocyanate and as an intermediate in the synthesis of dyestuffs, herbicides, and degreasers. p-Dichlorbenzene is used primarily as a moth repellant, a mildew control agent; space deodorant; and in insecticides, which accounts for 90% of the total production of this isomer. Information is not available concerning the production and use of m-DCB. However, it may occur as a contaminant of o-or p-DCB formulations. Both o-and p-isomers are produced almost entirely as by-products during the production of monochlorobenzene

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Carcinogenicity: 1,4-Dichlorobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental fate: Biological. In activated sludge, <0.1% degraded (mineralized) to carbon dioxide after 5 d (Freitag et al., 1985). When 1,4-dichlorobenzene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with gradual acclimation was followed by a deadaptive process in subsequent subcultures. At a concentration of 5 mg/L, 55, 61, 34, and 16% losses were observed after 7, 14, 21, and 28-d incubation periods, respectively. At a concentration of 10 mg/L, only 37, 54, 29, and 0% losses were observed after 7, 14, 21, and 28-d incubation periods, respectively (Tabak et al., 1981).
Surface Water. Estimated half-lives of 1,4-dichlorobenzene (1.5 μg/L) from an experimental marine mesocosm during the spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 18, 10, and 13 d, respectively (Wakeham et al., 1983).
Groundwater. Nielsen et al. (1996) studied the degradation of 1,4-dichlorobenzene in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine 1,4-dichlorobenzene concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life following a 22-d lag phase were 0.05/d and 13.86 d, respectively.
Under anaerobic conditions, 1,4-dichlorobenzene in a plume of contaminated groundwater was found to be very persistent (Barber, 1988).
Photolytic. Under artificial sunlight, river water containing 2 to 5 ppm of 1,4-dichlorobenzene photodegraded to chlorophenol and phenol (Mansour et al., 1989). A carbon dioxide yield of 5.1% was achieved when 1,4-dichlorobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Irradiation of 1,4-dichlorophenol in air containing nitrogen oxides gave 2,5-dichlorophenol (major product), 2,5-dichloronitrobenzene, 2,5-dichlorophenol, and 2,5-dichloro-4-nitrophenol (Nojima and Kanno, 1980). The sunlight irradiation of 1,4- dichlorobenzene (20 g) in a 100-mL borosilicate glass-stoppered Erlenmeyer flask for 56 d yielded 1,860 ppm 2′,4,5′-trichlorobiphenyl (Uyeta et al., 1976).
Chemical/Physical. Anticipated products from the reaction of 1,4-dichlorobenzene with ozone or OH radicals in the atmosphere are chlorinated phenols, ring cleavage products, and nitro compounds (Cupitt, 1980).

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Metabolic pathway: 1,4-Dichlorobenzene undergoes degradation by the Xanthobacter flavus 14p1 isolated from river sludge by selective enrichment with 1,4-dichlorobenzene, resulting in the degradation products 3,6-dichloro-cis- 1,2-dihydroxycyclohexa-3,5-diene and 3,6- dichlorocatechol. 2,5-Dichloromuconic acid and 2- chloromaleylacetic acid, as well as the decarboxylation product 2-chloroacetoacrylic acid, are identified after enzymatic conversion of 3,6-dichlorocatechol.

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Shipping: m-DCB: UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. United States DOT Regulated Marine Pollutant. UN3077 Environmentally hazardous substances, solis, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical NameRequired. UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

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Purification Methods: o-Dichlorobenzene is a common impurity. The p-isomer has been purified by steam distillation, crystallisation from EtOH or boiling MeOH, air-dried and dried in the dark under vacuum. It has also been purified by zone refining. [Beilstein 5 IV 658.]

Incompatibilities: For o-DCB and m-DCB: acid fumes, chlorides, strong oxidizers; hot aluminum, or aluminum alloys. For p-DCB: Strong oxidizers; although, incompatibilities for this chemical may also include other materials listed for o-DCB.

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. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

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