ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Hydrocarbon halides > Chlorobenzene
Chlorobenzene Chemical Properties
- Melting point:-45 °C (lit.)
- Boiling point:132 °C (lit.)
- Density 1.106 g/mL at 25 °C (lit.)
- vapor density 3.86 (vs air)
- vapor pressure 11.8 mm Hg ( 25 °C)
- refractive index n
- Flash point:75 °F
- storage temp. 2-8°C
- solubility water: soluble0.207 g/L at 20°C
- form Liquid
- color APHA: ≤30
- Relative polarity0.188
- OdorAlmond like odour
- explosive limit1.3-11%(V)
- Water Solubility 0.4 g/L (20 ºC)
- FreezingPoint -45.6℃
- λmaxλ: 288 nm Amax: 1.0
λ: 290 nm Amax: 0.40
λ: 300 nm Amax: 0.05
λ: 325 nm Amax: 0.04
λ: 360-400 nm Amax: 0.01
- Merck 14,2121
- BRN 605632
- Henry's Law Constant1.11, 1.54, 1.81, 2.80, and 3.79 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (EPICS-SPME, Dewulf et al., 1999)(x 10-3 atm?m3/mol)
- Exposure limitsTLV-TWA 75 ppm (～345 mg/m3) (ACGIH, MSHA, OSHA, and NIOSH); IDLH 2400 ppm.
- Stability:Stable. Incompatible with oxidizing agents. Flammable. Attacks some types of plastics, rubber and coatings.
- CAS DataBase Reference108-90-7(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzene, chloro-(108-90-7)
- EPA Substance Registry SystemChlorobenzene (108-90-7)
- Hazard Codes Xn,N,T,F
- Risk Statements 10-20-51/53-40-39/23/24/25-23/24/25-11
- Safety Statements 24/25-61-36/37-45-16-7
- RIDADR UN 1134 3/PG 3
- WGK Germany 2
- RTECS CZ0175000
- F 3-10
- Autoignition Temperature590 °C
- TSCA Yes
- HazardClass 3
- PackingGroup III
- HS Code 29039190
- Hazardous Substances Data108-90-7(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 2000 - 4000 mg/kg
Chlorobenzene Usage And Synthesis
- UsesManufacture of phenol, aniline, DDT; solvent for paint; color printing; dry cleaning industry.
- DescriptionChlorobenzene 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.
- 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.
- 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.
- manufacture of phenol, aniline, DDT; solvent for paints; heat transfer medium.
- 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.
- Chlorobenzene is a basic substance used in chemical syntheses with 95% of the quantity used converted in closed systems to intermediate and final products.
- It is used as a process solvent in the manufacture of three indigoid dyes and pigments. All the pigments and dyes are thioindigoid colors.
- 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.
- ToxicityThe 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.
- DescriptionChlorobenzene 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.
- Chemical Propertiescolourless 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.
- Chemical PropertiesChlorobenzene, 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.
- Physical propertiesClear, 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.
- UsesChlorobenzene is used as a solvent for paints,as a heat transfer medium, and in the manu facture of phenol and aniline.
- UsesChlorobenzene is a halogenated benzene used in chemical toxicity QSAR research for agricultural pollution.
- UsesMonochlorobenzene is used commercially as a solvent and to produce phenol and nitrochlorobenzenes.
- DefinitionChEBI: The simplest member of the class of monochlorobenzenes, that is benzene in which a single hydrogen has been substituted by a chlorine.
- DefinitionA 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
- General DescriptionA 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 ReactionsHighly flammable. Insoluble in water.
- Reactivity ProfileChlorobenzene 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. .
- HazardA possible carcinogen. Avoid inhalation and skin contact. Moderate fire risk. Explosive limits 1.8–9.6%.
- Health HazardIrritating 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.
- Fire HazardFlammable liquid; flash point (closed cup)
29°C (84°F); vapor pressure 8.8 torr at
20°C (68°F); autoignition temperature 638°C
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.
- Safety ProfileSuspected 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
- Potential ExposureChlorobenzene 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.
- CarcinogenicityChlorobenzene 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 FateBiological. 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
- ShippingUN1134 Chlorobenzene, Hazard Class: 3; Labels: 3-Flammable liquid.
- Purification MethodsThe 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.]
- Toxicity evaluationIn 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.
- IncompatibilitiesReacts 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 DisposalIncineration, 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.
Chlorobenzene Preparation Products And Raw materials
- Preparation Products4-Chlorobenzenesulfonyl chloride2-TERT-BUTYLPYRIDINE-4-CARBONITRILE2-ChloroacetophenoneAtrazinePhenyltrichlorosilane5-Bromothiophene-2-carbaldehyde5-CHLORO-3-METHYLBENZO[B]THIOPHENE6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE3-CHLOROBENZO[B]THIOPHENE-2-CARBOXAMIDEFluoxastrobin5-CHLOROBENZOTHIOPHENE5-DIMETHYLAMINO-THIOPHENE-2-CARBALDEHYDE3,4'-Dichlorodiphenyl etherMETHYL 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLATENaphthol AS-D3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide2,2'-(1,3,4-oxadiazole-2,5-diyl)bis[1-aminoanthraquinone] 2-Bromo-4-nitroimidazole3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE2,5-Thiophenedicarboxylic acidETHYL ALPHA-CHLOROPHENYLACETATEBaclofen4,4'-DDT3-Hydroxy-2-naphthoyl-ortho-phenetidide3-Hydroxy-N-naphthalen-1-ylnaphthalene-2-carboxamide3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID2-Chloro-1,3-dinitrobenzene3-CHLOROBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE2-THENOYLACETONITRILE2-Hydroxy-N-(4-methoxyphenyl)-11H-benzo[a]carbazole-3-carboxamidepigment yellow 155dimethyl 4-chloropyridine-2,6-dicarboxylate1-Benzyl-2-methyl-1H-imidazole3-(4-Chlorobenzoyl)propionic acid2-Chloroanthraquinone2-AMINO-5,6-DIMETHYLBENZOTHIAZOLENAPHTHOL AS-LT3-Hydroxy-4'-methoxy-2-naphthanilide4,4'-Dichlorodiphenyl sulfoneDICLOMEZINE
- Raw materialsHydrochloric acidBenzeneChlorineAluminum oxide 1,2-DichlorobenzeneFlow Cellp-DichlorobenzeneANHYDROUS FERRIC CHLORIDE
- 2,4-Dichlorobenzyl chloride Toluene PHENYL RESIN PHENYL VALERATE Phenyl salicylate Methylene Chloride O1-[3-(5-CHLORO-1,3-DIMETHYL-1H-PYRAZOL-4-YL)ACRYLOYL]-4-CHLOROBENZENE-1-CARBOHYDROXIMAMIDE CHLOROBENZENE-4-D1 N1-[4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)PHENYL]-4-CHLOROBENZENE-1-SULFONAMIDE N'1-[(5-CHLORO-1,3-DIMETHYL-1H-PYRAZOL-4-YL)METHYLIDENE]-2-CHLOROBENZENE-1-SULFONOHYDRAZIDE (R)-2-HYDROXY-2-METHYL(3-CHLOROBENZENE)PROPANOIC ACID (R)-2-HYDROXY-2-METHYL(4-CHLOROBENZENE)PROPANOIC ACID ETHYL (R)-2-HYDROXY-2-METHYL(4-CHLOROBENZENE)PROPANOATE N1-(2,2-DIETHOXYETHYL)-N1-(4-FLUOROPHENYL)-4-CHLOROBENZENE-1-SULFONAMIDE O1-(2-CHLOROACETYL)-4-CHLOROBENZENE-1-CARBOHYDROXIMAMIDE N'1-(2-CHLOROACETYL)-4-CHLOROBENZENE-1-CARBOHYDRAZIDE N'1-((5-[(4,5-DICHLORO-1H-IMIDAZOL-1-YL)METHYL]-2-FURYL)CARBONYL)-4-CHLOROBENZENE-1-SULFONOHYDRAZIDE (R)-2-HYDROXY-2-METHYL(3-CHLOROBENZENE)ACETIC ACID
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