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NIH U.S. National Library of Medicine National Center for Biotechnology Information PubChem logo OPENCHEMISTRYDATABASE Compound Summary for CID 10943 PubChem compound 1,3-DICHLOROBENZENE 1,3-DICHLOROBENZENE Vendors Pharmacology Literature Patents Bioactivities 1,3-DICHLOROBENZENE_small.png PubChem CID: 10943 Chemical Names: 1,3-DICHLOROBENZENE; M-Dichlorobenzene; 541-73-1; Meta-Dichlorobenzene; M-Dichlorobenzol; Benzene, 1,3-dichloro-; More... Molecular Formula: C6H4Cl2 Molecular Weight: 147.00196 g/mol InChI Key: ZPQOPVIELGIULI-UHFFFAOYSA-N UNII: 75W0WNE5FP Safety Summary: Laboratory Chemical Safety Summary (LCSS) Modify Date: 2016-04-02 Create Date: 2005-03-26 There are three dichlorobenzene isomers- 1,2-dichlorobenzene, 1,3-dichlorobenzene, and 1,4-dichlorobenzene. Dichlorobenzenes do not occur naturally. 1,2-Dichlorobenzene is a colorless to pale yellow liquid used to make herbicides. 1,3- Dichlorobenzene is a colorless liquid used to make herbicides, insecticides, medicine, and dyes. 1,4-Dichlorobenzene, the most important of the three chemicals, is a colorless to white solid with a strong, pungent odor. When exposed to air, it slowly changes from a solid to a vapor. Most people can smell 1,4- dichlorobenzene in the air at very low levels. 2D Structure 3D Conformer Names and Identifiers Chemical and Physical Properties Related Records Chemical Vendors Pharmacology and Biochemistry Use and Manufacturing Identification Safety and Hazards Toxicity Literature Patents Biomolecular Interactions and Pathways Biological Test Results Classification Information Sources 2D Structure 1,3-DICHLOROBENZENE.png 3D Conformer Names and Identifiers Computed Descriptors IUPAC Name 1,3-dichlorobenzene InChI InChI=1S/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4H InChI Key ZPQOPVIELGIULI-UHFFFAOYSA-N Canonical SMILES C1=CC(=CC(=C1)Cl)Cl Other Identifiers CAS 541-73-1 EC Number 208-792-1 ICSC Number 1095 RTECS Number CZ4499000 UN Number 2810 1993 UNII 75W0WNE5FP Wikipedia Wikipedia 1,3-dichlorobenzene Synonyms MeSH Synonyms 1,3-dichlorobenzene m-dichlorobenzene Depositor-Supplied Synonyms 1,3-DICHLOROBENZENE m-Dichlorobenzene 541-73-1 meta-Dichlorobenzene m-Dichlorobenzol Benzene, 1,3-dichloro- m-Phenylene dichloride Benzene, m-dichloro- Metadichlorobenzene m-Phenylenedichloride m-DCB 1,3-dichloro-benzene NSC 8754 RCRA waste no. U071 UNII-75W0WNE5FP CCRIS 4259 HSDB 522 CHEBI:36693 ZPQOPVIELGIULI-UHFFFAOYSA-N EINECS 208-792-1 2,4-dichlorobenzene AI3-15517 DSSTox_CID_2056 DSSTox_RID_76473 DSSTox_GSID_22056 1,3-Dichlorobenzene solution CAS-541-73-1 m-dichlorobenzen 3-dichlorobenzene MDCB PubChem13088 ACMC-209tea 1,3-bis(chloranyl)benzene AC1L1WA5 75W0WNE5FP SCHEMBL28140 M-DICHLOROBENZENE 99 KSC255M9B MLS001050090 35350_ALDRICH 40214_SUPELCO 48523_SUPELCO 48638_SUPELCO CHEMBL45235 113808_ALDRICH 36708_RIEDEL PARAGOS 530110 35350_FLUKA 36708_FLUKA NSC8754 MolPort-003-925-956 LABOTEST-BB LTBB002096 LTBB002096 ZINC388095 CS-B0931 NSC-8754 Tox21_202179 Tox21_300005 ANW-42368 LS-207 AKOS009031576 AS00251 MCULE-4362550696 RP21109 RTR-019159 TRA0127964 NCGC00091197-01 NCGC00091197-02 NCGC00091197-03 NCGC00253960-01 NCGC00259728-01 AJ-20426 AK114310 AN-21339 BC205103 CJ-03113 KB-78294 OR001079 SMR001216526 ZB011284 ST2414814 TR-019159 D0333 FT-0606649 FT-0657417 S0665 C19397 28316-EP2269986A1 28316-EP2287141A1 28316-EP2305655A2 28316-EP2314577A1 A830009 3B4-2898 I01-3651 J-503894 InChI=1/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4 UNII-F56X88UAJQ component ZPQOPVIELGIULI-UHFFFAOYSA-N 46536A91-5C63-4685-94E2-E2FAB9C3B34D 1,3-DICHLOROBENZENE (SEE ALSO: 1,2-DICHLOROBENZENE (95-50-1) & 1,4-DICHLOROBENZENE (106-46-7)) 63697-17-6 Chemical and Physical Properties Computed Properties Molecular Weight 147.00196 g/mol Molecular Formula C6H4Cl2 XLogP3 3.5 Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 0 Rotatable Bond Count 0 Exact Mass 145.969005 g/mol Monoisotopic Mass 145.969005 g/mol Topological Polar Surface Area 0 A^2 Heavy Atom Count 8 Formal Charge 0 Complexity 64.9 Isotope Atom Count 0 Defined Atom Stereocenter Count 0 Undefined Atom Stereocenter Count 0 Defined Bond Stereocenter Count 0 Undefined Bond Stereocenter Count 0 Covalently-Bonded Unit Count 1 Experimental Properties Physical Description COLOURLESS LIQUID. Liquid Color Colorless liquid Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 359 Boiling Point 173 deg C Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-150 173°C Melting Point -24.8 deg C Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-150 -24.8°C Flash Point 63°C 63°C closed cup Solubility Sol in ethanol, ether; very soluble in acetone Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-150 In water, 125 mg/L at 25 deg C Miller MM et al; J Chem Eng Data 29:184-90 (1984) in water: none Density 1.2884 at 20 deg C/4 deg C Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-150 (water = 1): 1.288 Vapor Density (air = 1): 5.1 Vapor Pressure 2.15 mm Hg at 25 deg C Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989. Vapour pressure kPa at 25°C: 0.286 0.286 kPa @ 25°C LogP log Kow = 3.53 Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 17 3.53 Auto-Ignition >500 deg C European Chemicals Bureau; IUCLID Dataset, 1,3-Dichlorobenzene (541-73-1) p.12 (2000 CD-ROM edition). Available from, as of January 10, 2008: http://esis.jrc.ec.europa.eu/ Decomposition When heated to decomposition it emits toxic /hydrogen chloride/ fumes. Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1174 Viscosity 1.044 mPa.s at 25 deg C Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-177 Heat of Vaporization 296.8 J/g Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V6: 89 (1993) Surface Tension 36.20 dynes/cm Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V6: 89 (1993) Kovats Retention Index Standard non-polar 975.4, 986.21, 985.1, 1002, 1014, 985, 990, 982, 1025, 1013.8, 1009, 985, 964, 1016, 1013, 1016, 964, 1000, 997, 964, 1004.1, 985.2, 991.2, 997.1, 988, 1005, 986, 982, 1011.1, 981, 981, 981, 982, 1004 Semi-standard non-polar 1022, 1014.97, 1015.34, 1017.77, 1018.92, 1020.9, 1002.37, 997.98, 999.87, 1017.4, 1020.06, 1027.05, 1027.35, 1022.5, 1022.5, 1036.2, 1004.07, 1013.3, 1024.65, 1058, 1007, 1011, 1014, 1022, 1005, 1024.8, 1006.8, 1047, 1021, 1045, 1002, 1002.6, 997, 162, 160.4 Standard polar 1417.7, 1438.32, 1445.33, 1446, 1451, 1453, 1455.4, 1474.1, 1415, 1415, 1434, 1409, 1414, 1477, 1455.6, 1418 Chemical Classes Volatile organic compounds Crystal Structures Crystal Structures: 1 of 2 CCDC Number 165223 Crystal Structure Data DOI:10.5517/cc5jxsc Associated Article DOI:10.1002/1522-2675(20010613)84:63.0.CO;2-M Crystal Structures: 2 of 2 CCDC Number 637752 Crystal Structure Data DOI:10.5517/ccpdmnb Associated Article DOI:10.1107/S0108768106046684 Spectral Properties Index of refraction: 1.5515 at 20 deg C/D Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-150 Intense mass spectral peaks: 146 m/z (100%), 148 m/z (64%), 111 m/z (37%), 75 m/z (22%) Hites, R.A. Handbook of Mass Spectra of Environmental Contaminants. Boca Raton, FL: CRC Press Inc., 1985., p. 70 IR: 5654 (Coblentz Society Spectral Collection) Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 825 UV: 1671 (Sadtler Research Laboratories Spectral Collection) Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 825 NMR: 8596 (Sadtler Research Laboratories Spectral Collection) Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 825 MASS: 818 (Atlas of Mass Spectral Data, John Wiley & Sons, New York) Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 825 GC-MS 1 of 4 NIST Number 291447 Library Main library Total Peaks 63 m/z Top Peak 146 m/z 2nd Highest 148 m/z 3rd Highest 111 Thumbnail Related Records Related Compounds with Annotation Related Compounds Same Connectivity 8 records Same Parent, Connectivity 50 records Same Parent, Exact 43 records Mixtures, Components, and Neutralized Forms 109 records Similar Compounds 274 records Similar Conformers 16510 records Substances Related Substances All 295 records Same 122 records Mixture 173 records Substances by Category Entrez Crosslinks PubMed 86 records Taxonomy 1 record Gene 1 record Chemical Vendors Pharmacology and Biochemistry Absorption, Distribution and Excretion The dichlorobenzenes may be absorbed through the lung, gastrointestinal tract, and intact skin. Relatively low water solubility and high lipid solubility favor their penetration of most membranes by diffusion, including pulmonary and GI epithelia, the brain, hepatic parenchyma, renal tubules, and the placenta. /Dichlorobenzenes/ USEPA; Ambient Water Quality Criteria Doc: Dichlorobenzenes p.C-14 (1980) EPA 440/5-80-039 Information on the quantitative absorption of 1,3-DCB in humans and animals is not available for any route of exposure; however, absorption of the compound can be inferred from studies that have detected 1,3-DCB or metabolites in the breast milk, blood, and fat of humans and in the bile and urine of exposed animals. Distribution is believed to be similar to the other DCB isomers, but data demonstrating this are not presently available. Similar to the other DCB isomers, 1,3-DCB is initially metabolized by cytochrome P-450 enzymes, followed by extensive conjugation, primarily to glutathione, has been reported. 1,3-DCB is eliminated mainly in the urine, similar to the other DCB isomers. U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Dichlorobenzenes p.202 (August 2006) PB2007-100672. Available from, as of January 7, 2008: http://www.atsdr.cdc.gov/toxpro2.html# Children can be exposed to DCBs prenatally, as indicated by the detection of all three isomers in placenta samples, as well as through breast feeding. 1,2-DCB concentrations measured in whole human milk range from 3 to 29 ppb. 1,3- and 1,4-DCB were detected together in whole human milk with mean and maximum concentrations of 6 and 75 ppb, respectively. These isomers were detected in milkfat samples at a mean concentration of 161 ppb and a maximum concentration of 4,180 ppb. 1,2-, 1,3-, and 1,4-DCB measured separately in whole human milk samples had concentrations of 9, <5, and 25 ppb, respectively, while the milk fat of these samples contained 230 ppb of 1,2-DCB and 640 ppb of 1,4-DCB. U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Dichlorobenzenes p.12 (August 2006) PB2007-100672. Available from, as of January 18, 2008: http://www.atsdr.cdc.gov/toxpro2.html# Metabolism/Metabolites M-Dichlorobenzene yields N-acetyl-S-(2,4-dichlorophenyl)-L-cysteine, 2,4-dichlorophenol, and 3,5-dichlorophenol in rabbit. /from table/ Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. D-15 When fed to rabbits, m-dichlorobenzene yielded glucuronides (31%, sulfates (11%), mercapturic acid (9%) and catechols (4%). ...2,4-Dichlorophenylmercapturic acid and 3,5-dichlorocatechol were also observed... Menzie, C.M. Metabolism of Pesticides, Update II. U.S. Department of the Interior, Fish Wildlife Service, Special Scientific Report - Wildlife No. 2l2. Washington, DC: U.S. Government Printing Office, 1978., p. 95 1,3-Dichlorobenzene was reported to be among several metabolites of gamma-pentachloro-1-cyclohexane in corn and pea seedlings. USEPA; Ambient Water Quality Criteria Doc: Dichlorobenzene p.C-10 (1980) EPA 440/5-80-039 The S-containing metabolites of m-dichlorobenzene (m-DCB) were identified by using gas chromatography-mass spectrometry and disposition of m-DCB metabolites studied. In the blood, urine and feces of rats dosed with m-DCB, 2,4- and 3,5-dichlorophenyl methylsulfoxide and 3,5- and 2,4-dichlorophenyl methanesulfonate emerged, while their possible precursors, 3,5- and 2,4-dichlorophenyl methyl sulfide were not detected in the blood, urine, and feces. However, after heating the alkalinized urine and feces, the methyl sulfides appeared. ... Abstract: PubMed Kimura R et al; J Pharmacobio-Dyn 7 (4): 234-45 (1984) 1,2,4-Trichlorobenzene (TCB) was reductively converted into monochlorobenzene (MCB) via dichlorobenzenes on incubation with intestinal contents of rats. When the amounts of MCB produced from o-DCB, m-DCB, or p-DCB as substrates were compared, the amount was the least in the case of o-DCB. This was consistent with the finding that o-DCB tended to accumulate more than the other isomers. The mechanism of the reductive dechlorination of aromatic compounds is not well understood. Tsuchiya T, Yamaha T; Agric Biol Chem 47 (5): 1163-5 (1983) The increases in the hepatic microsomal aminopyrine N-demethylase activity and in the content of cytochrome p450 produced by m-dichlorobenzene (m-DCB) occurred after increases in the hepatic concentration of 3,5-dichlorophenyl methyl sulfone, a minor metabolite. The extent of increases in aminopyrine N-demethylase activity and in the content of cytochrome p450 at 48 hr after administration of 200 mg/kg (1.36 mmol/kg) of m-DCB was almost equal to that 72 hr after the ip administration of 25 umol/kg of the sulfone. m-DCB in liver was not detectable at that time, and the concentration of sulfone was 63 to 70% of that 48 to 72 hr after the ip administration of 50 umol/kg of sulfone. Administration of m-DCB (200 mg/kg) produced a significant reduction in hexobarbital sleeping time, but this reduction was less than that produced by administration of the sulfone (50 umol/kg). The protein band patterns by sodium dodecyl sulfate-polyacrylamide gel electrophoresis of the microsomes from rats treated with the sulfone and m-DCB were similar to those of phenobarbital-treated rats but were different from those of 3-methylcholanthrene-treated rats. The sulfone showed type I interaction with the cytochrome p450 (Ks, 0.17 mM). The sulfone was formed from the sulfide but reduction of the sulfone was not observed when it was incubated in a hepatic microsomal preparation. The pattern of induction by the sulfone and m-DCB was similar to that by phenobarbital and differed from that by 3-methylcholanthrene. From these results, 3,5-dichlorophenyl methyl sulfone is considered to be a major contributing factor of the inducing activity of m-DCB and to be a potent phenobarbital like inducer. Abstract: PubMed Kimura R; Toxicol Appl Pharmacol 78 (2): 300-9 (1985) ...In rat liver slices, the majority (~70%) of 1,3-DCB was found conjugated to glutathione, or as a cysteine conjugate, with only small amounts of the glucuronide or sulfate detected. In human liver slices, the pattern was different, with approximately equal distribution (~40% each) of glucuronide and glutathione conjugates, and ~20% of the metabolites as the sulfate. Human liver slices metabolized greater amounts of 1,3-DCB than did slices from F344 or Sprague-Dawley rats. Human liver slices formed 2-9-fold greater levels of glucuronide conjugates, 1-4-fold greater levels of sulphatase conjugates, and 1-4-fold greater levels of glutathione/cysteine conjugates of 1,3-DCB than rat liver slices. U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Regis

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