2,3-Dichlorobenzyl chloride
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2,3-Dichlorobenzyl chloride
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CAS No:
3290-01-5
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Formula:
C7H5Cl3
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Chemical Name:
2,3-Dichlorobenzyl chloride
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Synonyms:
Benzene,1,2-dichloro-3-(chloromethyl)-;Toluene,α,2,3-trichloro-;1,2-Dichloro-3-(chloromethyl)benzene;2,3-Dichlorobenzyl chloride;2,3-Dichloro-1-(chloromethyl)benzene
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CAS No:
2,3-Dichlorobenzyl chloride Basic Attributes
195.47
195.47
221-947-8
B40AZJ572L
DTXSID8052061
COLORLESS LIQUID
2903999090
Characteristics
0
3.55
Clear colorless liquid
1.415-1.42 @ 25 DEG C/15 DEG C
36.0 °C
255 °C
160.2±18.8 °C
1.563
soluble in alcohol, ether, acetone. Slightly soluble in heptane. Insoluble in water.
Penetrating odor
Safety Information
IRRITANT, LACHRYMATOR
1760
34-22
45-36/37/39-26
C
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
H314
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Contamination with metals in the presence of moisture may cause rapid decomposition, liberating heat, hydrogen chloride, and hydrogen which can result in explosive pressure build-up in closed systems.
ITC/USEPA; Information Review #354 (Draft) Tri & Dichlorobenzyl Chlorides (1983)
|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory.
For line and vessel entry without decontamination and for accidents, maintenance and operational personnel employ full face and respiratory protection. In addition, all personnel carry disposable mouth bite respirators for emergency escape.
The manufacturing process is designed so that a local exhaust ventilation system (i.e. suction hosing) controls emissions in the workplace during product drumming, catalyst addition, and emissions which may arise through accidental release.|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.
Toxicity
LD50 Rat male oral 1080 mg/kg
/Individuals who suffer from/ skin, liver, kidney, or chronic respiratory disease, will be at an increased risk if they are exposed to chlorobenzenes. /Chlorobenzenes/
Dichlorobenzyl chloride's production and use as an intermediate for organic chemicals, pharmaceuticals, and dyes, and as an insecticide(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Dichlorobenzyl chloride is expected to hydrolyze in moist soils(SRC) based upon the rapid hydrolysis of the structurally similar benzyl chloride; at pH 7 and 25 °C the hydrolysis half-life is approx 15 hours(1). Volatilization, adsorption, and biodegradation are not expected to be important fate processes in moist soils because of hydrolysis(SRC). Dichlorobenzyl chloride is not expected to volatilize from dry soil surfaces based upon estimated vapor pressure for the six isomers ranging from 0.024 to 0.033 mm Hg(SRC), determined from a fragment constant method(2).|AQUATIC FATE: Dichlorobenzyl chloride is expected to hydrolyze in aquatic environments(SRC) based upon the rapid hydrolysis of the structurally similar benzyl chloride; at pH 7 and 25 °C the hydrolysis half-life is approx 15 hours(1). Volatilization from water surfaces, adsorption to suspended solids and sediments, biodegradation, and bioconcentration are not expected to be an important fate process in aquatic systems for the parent compound because of rapid rate of hydrolysis(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlorobenzyl chloride, which has estimated vapor pressures for the six isomers ranging from 0.024 to 0.033 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dichlorobenzyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); estimated half-lives for this reaction in air range from 12 to 21 days for the six isomers(3,SRC).
Rate constants, estimated using a structure estimation method(1), for the vapor-phase reaction of the six isomers of dichlorobenzyl chloride with photochemically-produced hydroxyl radicals range from 7.8X10-13 to 1.4X10-12 cu cm/molecule-sec at 25 °C(SRC). These rate constants correspond to atmospheric half-lives ranging from 12 to 21 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Hydrolysis is expected to be an important removal process(SRC), based upon a reported hydrolysis half-life of 15 hours at 25 °C and pH 7 for the structural analog benzyl chloride(2).
Based upon the rapid hydrolysis of the structurally similar benzyl chloride in aqueous environments(1), bioconcentration of dichlorobenzyl chloride in aquatic organisms is not expected to be an important fate process(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for dichlorobenzyl chloride can be estimated to be about 1,400(SRC). According to a classification scheme(2), this estimated Koc value suggests that dichlorobenzyl chloride is expected to have low mobility in soil(SRC). Hydrolysis of dichlorobenzyl chloride is expected in moist soils(SRC), based upon a reported hydrolysis half-life of 15 hours for the structural analog benzyl chloride(3).
Based upon the rapid hydrolysis of the structurally similar benzyl chloride in aqueous environments(1), volatilization of dichlorobenzyl chloride from water and moist soil surfaces is not expected to be an important fate process(SRC). Dichlorobenzyl chloride is not expected to volatilize from dry soil surfaces based upon estimated vapor pressure for the six isomers ranging from 0.024 to 0.033 mm Hg(SRC), determined from a fragment constant method(2).
Occupational exposure to dichlorobenzyl chloride may occur through inhalation and dermal contact with this compound at workplaces where dichlorobenzyl chloride is produced or used. (SRC)
Drug Information
Final product assays approx 95% dichlorobenzyl chloride with the remaining 5% a mixture of various higher boiling chlorination by-products.
2,3-Dichlorobenzyl chloride Use and Manufacturing
2,4- and 3,4-dichlorobenzyl chloride are manufactured by side-chain chlorination of the appropriate chlorotoluene. 3,4-Dichlorobenzyl chloride containing some 2,3-dichlorobenzyl chloride is produced by the chloromethylation of o-dichlorobenzene in oleum solution.
Intermediate for organic chemicals, pharmaceuticals, & dyes; intermediate for insecticide|Intermediate in the manufacture of benzyl ammonium quarternary algicides used in swimming pool formulations.
Stauffer produces less than 300,000 lb annually.
Benzene, dichloro(chloromethyl)-: INACTIVE|Monsanto and Tenneco reported in 1983 that they no longer manufacture the compound therefore Stauffer may be the sole domestic producer of dichlorobenzyl chloride.|Manufactured in a batch type process involving 2 distinct chlorination and fractionation steps carried out in closed vessels.
Computed Properties
Molecular Weight:195.5
XLogP3:3.6
Rotatable Bond Count:1
Exact Mass:193.945683
Monoisotopic Mass:193.945683
Heavy Atom Count:10
Complexity:105
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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