1,3-Dichlorobenzene

1,3-Dichlorobenzene Basic information
Product Name:1,3-Dichlorobenzene
Synonyms:Benzene, M-dichloro- (8CI);NSC 8754;Twochlorobenzene;1,3-Dichlorobenzene puriss., >=99.0% (GC);1.3-Dichlorobe;Benzene, m-dichloro-;Benzene,1,3-dichloro-;Benzene,m-dichloro-
CAS:541-73-1
MF:C6H4Cl2
MW:147
EINECS:208-792-1
Product Categories:Alphabetic;Pesticides&Metabolites;Alpha Sort;D;DAlphabetic;DIA - DIC;Volatiles/ Semivolatiles;Aryl;C6;Halogenated Hydrocarbons;Chlorobenzene Series;Organics;Analytical Chemistry;Standard Solution of Volatile Organic Compounds for Water & Soil Analysis;Standard Solutions (VOC);Pesticides intermediate
Mol File:541-73-1.mol
1,3-Dichlorobenzene Structure
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.)
Fp 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
LogP3.53 at 22℃
CAS DataBase Reference541-73-1(CAS DataBase Reference)
IARC3 (Vol. 73) 1999
NIST Chemistry ReferenceBenzene, 1,3-dichloro-(541-73-1)
EPA Substance Registry Systemm-Dichlorobenzene (541-73-1)
Safety Information
Hazard Codes Xn,N,T,F
Risk Statements 22-51/53-39/23/24/25-23/24/25-11
Safety Statements 61-45-36/37-16-7
RIDADR UN 3082 9/PG 3
WGK Germany 2
RTECS CZ4499000
Autoignition Temperature>500 °C
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29036990
Hazardous Substances Data541-73-1(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 580 mg/kg
MSDS Information
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1,3-Dichlorobenzene Usage And Synthesis
Chemical PropertiesThere are three isomeric forms of dichlorobenzene (DCB): m-DCB is a flammable liquid and vapor.
Physical properties1,3-Dichlorobenzene is a clear, colorless liquid with a disinfectant or musty-type odor. Soluble in alcohol, ether, insoluble in water. 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).
Uses1,3-Dichlorobenzene is used in organic synthesis that can synthesize fungicides imazalil, propiconazole, epiconazole, and insecticides insectaphos. It is also used in the synthesis of 1,2-diaminobenzene, in addition, it is also used as a solvent in the fields of dyes, medicine, resin, rubber and so on.
Uses1,3-Dichlorobenzene is used in medicine, and dyes. And it is also used to study the effect of solvent vapor pressure on the vertical nanowire of C60 molecules1. 1,3-Dichlorobenzene, a chlorinated aromatic hydrocarbon, can be detected in environmental samples using an advanced Fourier transform infrared spectroscopy-attenuated total reflectance (FTIR-ATR) sensor.
Application1,3-Dichlorobenzene was used to study the effect of solvent vapor pressure on the vertical nanowire of C60 molecules. 1,3-Dichlorobenzene, a chlorinated aromatic hydrocarbon, can be detected in environmental samples using an advanced Fourier transform infrared spectroscopy-attenuated total reflectance (FTIR-ATR) sensor.
DefinitionChEBI: 1,3-dichlorobenzene is a dichlorobenzene carrying chloro substituents at positions 1 and 3. Used as a fumigant, insecticide, and chemical intermediate.
Preparation1,3-Dichlorobenzene is prepared from o-chloroaniline through diazotization and displacement reaction.
Add o-chloroaniline and hydrochloric acid into the reaction pot, mix evenly below 25°C, cool to 0°C, drop in sodium nitrite solution, control the temperature at 0-5°C, stop adding when the potassium iodide starch indicator turns blue, and obtain diazonium salt solution. Then add the diazonium salt solution into the hydrochloric acid solution of cuprous chloride at 0~5℃, stir well, heat up to 60~70℃ and react for 1h, after cooling, let stand for stratification, and use 5% sodium hydroxide for the oil layer. Repeated washing with water, dehydration with anhydrous calcium chloride, fractional distillation, and collection of fractions at 177-183 °C to obtain the product 1,3-dichlorobenzene.
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.
Flammability and ExplosibilityFlammable
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
2,3,6-TRICHLOROANISOLE CARBONIC ACID TERT-BUTYL 2,4,5-TRICHLOROPHENYL ESTER cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl-4-methylbenzenesulphonate 2,4,5,6-TETRACHLORO-M-XYLENE 2,5-BIS(DICHLOROMETHYL)-1,4-DICHLOROBENZENE 95+%,2,5-BIS(DICHLOROMETHYL)-1,4-DICHLOROBENZENE 95+% 4-BROMOFLUOROBENZENE & 1,2-DICHLOROBENZENE-D4,4-BROMOFLUOROBENZENE & 1,2-DICHLOROBENZENE-D4 LEPTOMYCIN B MIXTURE PHENOL/1,2-DICHLOROBENZENE, 1:1 W/W, EXTRA PURE,MIXTURE PHENOL/1,2-DICHLOROBENZENE, 1:1 W/W, EXTRA PURE N1-(2-CHLOROETHANIMIDOYL)-3,5-DICHLOROBENZENE-1-SULPHONAMIDE,N1-(2-CHLOROETHANIMIDOYL)-3,5-DICHLOROBENZENE-1-SULPHONAMIDE Tecloftalam p-Dichlorobenzene N1-(2-CHLOROETHANIMIDOYL)-3,4-DICHLOROBENZENE-1-SULPHONAMIDE,N1-(2-CHLOROETHANIMIDOYL)-3,4-DICHLOROBENZENE-1-SULPHONAMIDE 4,5-dichlorobenzene-1,3-disulphonamide,4,5-dichlorobenzene-1,3-disulphonamide O1-(2-CHLOROACETYL)-2,3-DICHLOROBENZENE-1-CARBOHYDROXIMAMIDE, TECH,O1-(2-CHLOROACETYL)-2,3-DICHLOROBENZENE-1-CARBOHYDROXIMAMIDE, TECH 1 2-DICHLOROBENZENE-D4 1X1ML MEOH 20&,1 2-DICHLOROBENZENE-D4 1X1ML MEOH 20& DICHLOFENTHION 1.2-DICHLOROBENZENE SOLUTION 100UG/ML IN METHANOL 1ML,1.2-DICHLOROBENZENE SOLUTION 100UG/ML IN METHANOL 1ML 1,2-DICHLOROBENZENE-D4 & FLUOROBENZENE,1,2-DICHLOROBENZENE-D4 & FLUOROBENZENE

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