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1,3-Dichlorobenzene

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1,3-Dichlorobenzene Basic information
1,3-Dichlorobenzene Chemical Properties
  • Melting point:-25--22 °C (lit.)
  • Boiling point:172-173 °C (lit.)
  • Density 1.288 g/mL at 25 °C (lit.)
  • vapor pressure 5 mm Hg ( 38.8 °C)
  • refractive index n20/D 1.546(lit.)
  • Flash point:146 °F
  • storage temp. 2-8°C
  • solubility Difficult to mix.
  • form Liquid
  • color Clear colorless to slightly yellow
  • OdorPleasant odor
  • Water Solubility 0.0123 g/100 mL (25 ºC)
  • FreezingPoint -24℃
  • Merck 14,3055
  • BRN 956618
  • Henry's Law Constant2.14 at 20.00 °C (inert gas stripping, Hovorka and Dohnal, 1997)
  • Stability:Stability Combustible. Incompatible with strong oxidizing agents, aluminium, aluminium alloys. Moisture-sensitive.
  • InChIKeyZPQOPVIELGIULI-UHFFFAOYSA-N
  • CAS DataBase Reference541-73-1(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzene, 1,3-dichloro-(541-73-1)
  • IARC3 (Vol. 73) 1999
  • EPA Substance Registry Systemm-Dichlorobenzene (541-73-1)
Safety Information
MSDS
1,3-Dichlorobenzene Usage And Synthesis
  • Chemical Propertiescolourless liquid
  • Chemical PropertiesThere are three isomeric forms of dichlorobenzene (DCB): m-DCB is a flammable liquid and vapor.
  • Physical propertiesClear, colorless liquid with a disinfectant or musty-type odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 170 and 177 μg/L, respectively. At 25 °C, the lowest concentration at which a taste was detected was 190 μg/L, respectively (Young et al., 1996).
  • UsesFumigant and insecticide; organic synthesis.
  • DefinitionChEBI: A dichlorobenzene carrying chloro substituents at positions 1 and 3.
  • Synthesis Reference(s)The Journal of Organic Chemistry, 48, p. 250, 1983 DOI: 10.1021/jo00150a020
  • General DescriptionColorless liquid. Sinks in water.
  • Air & Water Reactions1,3-Dichlorobenzene is sensitive to moisture. Insoluble in water.
  • Reactivity Profile1,3-Dichlorobenzene is incompatible with oxidizing agents and aluminum and its alloys. Above the flash point, explosive vapor-air mixtures may be formed.
  • Health HazardINHALATION: Causes headache, drousiness, unsteadiness. Irritating to mucous membranes. EYES: Severe irritation. SKIN: Severe irritation. INGESTION: Irritation of gastric mucosa, nausea, vomiting, diarrhea, abdominal cramps and cyanosis.
  • Fire HazardSpecial Hazards of Combustion Products: Irritating vapors including hydrogen chloride are produced.
  • Safety ProfileModerately toxic by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl-. See also oDICHLOROBENZENE and p DICHLOROBENZENE.
  • Potential ExposureThe 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
  • Environmental FateBiological. When 1,3-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, 59, 69, 39, and 35% losses were observed after 7, 14, 21, and 28-d incubation periods, respectively. At a concentration of 10 mg/L, percent losses were virtually unchanged. After 7, 14, 21, and 28-d incubation periods, percent losses were 58, 67, 31, and 33, respectively (Tabak et al., 1981).
    Photolytic. The sunlight irradiation of 1,3-dichlorobenzene (20 g) in a 100-mL borosilicate glass-stoppered Erlenmeyer flask for 56 d yielded 520 ppm trichlorobiphenyl (Uyeta et al., 1976).
    Chemical/Physical. Anticipated products from the reaction of 1,3-dichlorobenzene with atmospheric ozone or OH radicals are chlorinated phenols, ring cleavage products, and nitro compounds (Cupitt, 1980). Based on an assumed base-mediated 1% disappearance after 16 d at 85 oC and pH 9.70 (pH 11.26 at 25 oC), the hydrolysis half-life was estimated to be >900 yr (Ellington et al., 1988). 1,3-Dichlorobenzene (0.17–0.23 mM) reacted with OH radicals in water (pH 8.7) at a rate of 5.0 x 109/M·sec (Haag and Yao, 1992).
  • Shippingm-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
  • Purification MethodsWash it with aqueous 10% NaOH, then with water until neutral, dry and distil it. Conductivity material (ca 10-10 mhos) has been prepared by refluxing over P2O5 for 8hours, then fractionally distilling, and storing with activated alumina. m-Dichlorobenzene dissolves rubber stoppers. [Beilstein 5 IV 657.]
  • IncompatibilitiesFor 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 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. 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
1,3-Dichlorobenzene Preparation Products And Raw materials
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