4-Chlorobenzyl chloride
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4-Chlorobenzyl chloride
structure -
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CAS No:
104-83-6
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Formula:
C7H6Cl2
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Chemical Name:
4-Chlorobenzyl chloride
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Synonyms:
Benzene,1-chloro-4-(chloromethyl)-;Toluene,p,α-dichloro-;1-Chloro-4-(chloromethyl)benzene;p,α-Dichlorotoluene;p-Chlorobenzyl chloride;α,p-Dichlorotoluene;4-Chlorobenzyl chloride;α,4-Dichlorotoluene;(4-Chlorophenyl)methyl chloride;p-Chlorophenylmethyl chloride;1-(Chloromethyl)-4-chlorobenzene;NSC 34032;4-Chloro-1-(chloromethyl)benzene;4-Chloromethylchlorobenzene
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CAS No:
Description
4-Chlorobenzyl Chloride is a benzylchloride derivative used in the preparation of various biologically active compounds such as bronchodilators and antibacterial agents.
4-Chlorobenzyl chloride Basic Attributes
161.03
161.03
471558
203-242-7
Q9HS4N7D3M
34032
2235
DTXSID4051530
COLORLESS LIQUID|Colorless needles
2903999090
Characteristics
0
3.18
Colorless to white Crystalline Low Melting Solid
1.388 g/cm3 @ Temp: 20 °C
31 °C
223 °C
208 °F
1.547
insoluble
Store at RT.
0.147mmHg at 25°C
Rat-unreported LD50: 1075 mg/kg; Mouse-unreported LD50: 1156 mg/kg
Open flame is flammable; heat decomposes toxic chloride and nitrogen oxide gas; emits poisonous chloride mist in contact with water
UV: 206 (Sadtler Research Laboratories Spectral Collection) /Benzyl chloride, 2-chloro/
Safety Information
III
6.1
UN 3427 6.1/PG 3
2
34-51/53-20/21/22-52/53-43-22
26-36/37/39-45-29-61-36/37
XT0720000
C,N,Xn
The warehouse is ventilated, low temperature and dry; stored and transported separately from water-containing items
Corrosive/Lachrymatory
Explosive when mixed with air
Stable under normal temperatures and pressures.
P273-P280
H302 + H312 + H332-H317-H411
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.
UN 2235/3427
|Danger|H302+H312+H332 (53.68%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P337+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 95 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P312, P321, P322, P330, P333+P313, P363, P403+P233, P405, and P501
SLIGHT, WHEN EXPOSED TO HEAT OR FLAME /4-CHLOROTOLUENE/
Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide, or dry chemical. /4-Chlorotoluene/
AVOID PROLONGED BREATHING OF VAPOR. USE WITH ADEQUATE VENTILATION. /4-CHLOROTOLUENE/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /4-Chlorotoluene/|Personnel protection: Avoid breathing vapors. Keep upwind. Wear boots, protective gloves, and goggles. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /4-Chlorotoluene/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chlorobenzyl chlorides; Chlorobenzyl chlorides, liquid; Chlorobenzyl chlorides, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorobenzyl chlorides; Chlorobenzyl chlorides, liquid; Chlorobenzyl chlorides, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Chlorobenzyl chlorides; Chlorobenzyl chlorides, liquid; Chlorobenzyl chlorides, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chlorobenzyl chlorides; Chlorobenzyl chlorides, liquid; Chlorobenzyl chlorides, solid/|For more DOT Emergency Guidelines (Complete) data for 1-CHLORO-4-CHLOROMETHYLBENZENE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
IRRITATING TO SKIN & EYES.
The major hazards encountered in the use and handling of 1-chloro-4-chloromethylbenzene stem from its toxicologic properties. Exposure to this colorless liquid occurs primarily in the occupational setting from its use as an intermediate in the synthesis of organic chemicals, pharmaceuticals, and dyes. Because this material is capable of causing irritation to the skin and eyes, persons involved with 1-chloro-4-chloromethylbenzene should wear boots, protective gloves, and goggles, at a minimum. When entering a contaminated area, also wear a full-face mask self-contained breathing apparatus which provides eye protection. Broken packages containing this substance should not be handled without protective equipment. Washing away any material which may have contacted the body with copious amounts of water, or soap and water is also recommended. This substance is normally stable, even under fire exposure conditions; requiring moderate heating for ignition to occur. Normal procedures may be used to fight a 1-chloro-4-chloromethylbenzene fire; extinguishing with "alcohol" foam, CO2, or dry chemical agents. Water also may be used in flooding quantities as a fog or spray (solid streams may be ineffective) to extinguish the fire and cool containers. The latter should be done from as far a distance as possible. This substance should be stored away from sparks, flames, and other sources of ignition. Containers of 1-chloro-4-chloromethylbenzene may be shipped by air, rail, road, or water, and should be affixed with labels stating, "Keep Away From Food". Regulatory requirements of the DOT should be consulted before transport. For large 1-chloro-4-chloromethylbenzene spills, use water spray to knock down vapor; keeping material out of water sources and sewers by diking, if necessary. Prior to implementing land diposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.
Toxicity
moderately toxic
/Individuals who suffer from/ skin, liver, kidney, or chronic respiratory disease, will be at an increased risk if they are exposed to chlorobenzenes. /Chlorobenzenes/
1-Chloro-4-chloromethylbenzene's use as an intermediate for organic chemicals, pharmaceuticals, and dyes(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,300(SRC), determined from a log Kow of 3.18(2) and a regression-derived equation(3), indicates that 1-chloro-4-chloromethylbenzene is expected to have low mobility in soil(SRC). Volatilization of 1-chloro-4-chloromethylbenzene from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 3.4X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Hydrolysis may occur in moist soils based upon an estimated hydrolysis half-life of 25.5 hours at 25 °C(SRC) from this compound's experimental activation energy(5). The potential for volatilization of 1-chloro-4-chloromethylbenzene from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 1.9 mm Hg(SRC), determined from a fragment constant method(6). Volatilization from soil surfaces may be attenuated by adsorption(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,300(SRC), determined from a log Kow of 3.18(2) and a regression-derived equation(3), indicates that 1-chloro-4-chloromethylbenzene is expected to adsorb to suspended solids and sediment in water(SRC). 1-Chloro-4-chloromethylbenzene may volatilize from water surfaces(3,SRC) based upon an estimated Henry's Law constant of 3.4X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake(3) are 7.0 hours and 6.0 days, respectively(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 3.3 days ignoring adsorption(5); when considering maximum adsorption the volatilization half-life increases to 9.9 days(5). According to a classification scheme(6), an estimated BCF of 150(3,SRC), from a log Kow(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Hydrolysis is expected to be an important process in aquatic systems based upon an estimated hydrolysis half-life of 25.5 hours at 25 °C(SRC) from this compound's experimental activation energy(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chloro-4-chloromethylbenzene, which has an estimated vapor pressure of 1.9 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chloro-4-chloromethylbenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 days(3,SRC). 1-Chloro-4-chloromethylbenzene has an adsorption band at 275 nm that extends to about 295 nm(4), suggesting 1-chloro-4-chloromethylbenzene may undergo direct photolysis(SRC).
The rate constant for the vapor-phase reaction of 1-chloro-4-chloromethylbenzene with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). 1-Chloro-4-chloromethylbenzene has an adsorption band at 275 nm that extends to about 295 nm(2), suggesting 1-chloro-4-chloromethylbenzene may potentially undergo direct photolysis(SRC). Hydrolysis rate constants of 5.69X10-5/sec and 3.35X10-4/sec were measured at 42.86 °C and 60.44 °C, respectively(3); these rate constants correspond to hydrolysis half-lives of 3.4 hours and 0.57 hours at 42.86 °C and 60.44 °C, respectively(SRC). A hydrolysis half-life of 25.5 hr(SRC) at 25 °C was extrapolated using the experimental activation energy(3).
An estimated BCF of 150 was calculated for 1-chloro-4-chloromethylbenzene(SRC), using a log Kow of 3.18(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high. However, bioconcentration may be attenuated by hydrolysis based upon a hydrolysis half-life of 25.5 hours at 25 °C(SRC), estimated from this compound's experimental activation energy(4).
The Koc of 1-chloro-4-chloromethylbenzene is estimated as approximately 1,300(SRC), using a log Kow of 3.18(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-chloro-4-chloromethylbenzene is expected to have low mobility in soil.
The Henry's Law constant for 1-chloro-4-chloromethylbenzene is estimated as 3.4X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-chloro-4-chloromethylbenzene is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 7.0 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 6.0 days(2,SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 3.3 days ignoring adsorption(3); when considering maximum adsorption the volatilization half-life increases to 9.9 days(3). 1-Chloro-4-chloromethylbenzene's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1-chloro-4-chloromethylbenzene from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 1.9 mm Hg(SRC), determined from a fragment constant method(4).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,961 workers (763 of these are female) are potentially exposed to 1-chloro-4-chloromethylbenzene in the US(1). Occupational exposure to 1-chloro-4-chloromethylbenzene may occur through inhalation and dermal contact with this compound at workplaces where 1-chloro-4-chloromethylbenzene is used(SRC).
Drug Information
YIELDS P-CHLOROBENZOIC ACID & PROBABLY S-(P-CHLOROBENZYL)-L-CYSTEINE IN RABBIT. /FROM TABLE/
Twenty dichloromethyl compounds have been tested as potential mechanism based inactivators of the major phenobarbital inducible isozyme of rat liver cytochrome p450 in a reconstituted system. With the exception of dichloromethane and dichloroacetamide, all the compounds decreased the ethoxycoumarin deethylase activity of the enzyme in a time and NADPH dependent manner.
1-chloro-4-(chloromethyl)benzene
4-Chlorobenzyl chloride Use and Manufacturing
The preparation method can use p-chlorotoluene, sulfuryl chloride and benzoyl peroxide as catalysts for chlorination, the reaction temperature is 85°C, the reaction is stirred for 2 hours, and post-treatment can be used to obtain p-chlorochlorobenzyl chloride. It can also be heated to 100 ℃ with p-chlorotoluene, photo-chlorinated with ultraviolet radiation, the reaction temperature is 135 ~ 140 ℃, a certain amount of chlorine gas is introduced, the reaction time is about 5h, the water layer is distilled under reduced pressure, and the collection is 126 ~ 148 ℃/8 ~13.3kPa crude fraction, and then rectification, collecting 80~84℃/160Pa fraction to p-chlorochlorobenzyl, yield 87%. In addition, p-chlorotoluene can also be used as a raw material, and azobisisobutyronitrile is added as a catalyst in an inert solvent. Chlorine gas is chlorinated under reflux under reflux. After the reaction is completed, the solvent is distilled off, and then the product is distilled under reduced pressure. Chlorobenzyl.
4-Chlorobenzyl Chloride is a benzylchloride derivative used in the preparation of various biologically active compounds such as bronchodilators and antibacterial agents.
Benzene, 1-chloro-4-(chloromethyl)-: ACTIVE|THE ALGICIDE, 1-(4-CHLOROBENZYL)-2-METHYLAZIRIDINE, IS PREPARED BY REACTION OF 4-CHLOROBENZYL CHLORIDE WITH 2-METHYLAZIRIDINE IN METHANOL AT ROOM TEMP IN PRESENCE OF POTASSIUM CARBONATE.
Analyte: Benzyl chloride; Matrix: air; Procedure: Gas chromatography, flame ionization detector; Desorption: 1 ml CS2, stand 30 min; Range: 0.005-0.15 mg/samp; Precision: 0.033; Est LOD: 0.01 mg/samp; Interferences: none /Hydrocarbons, halogenated, Benzyl chloride/
A method was developed to analyze rat tissue, fat and blood for some chlorinated compounds found in an extract soil from an industrial waste cite. Extraction with hexane and ethyl ether-hexane (1 + 1) was followed by concentration over steam, and gas chromatographic analysis with an electron detector. Volatile compounds were analyzed in a glass column coated with 6% SP-2100 plus 4% OV-11 on Chromosorb W. Semivolatile compounds, chlorinated compounds, and pesticides were analyzed in a 70 m glass capillary column coated with 5% OV-101. Phenols were analyzed in a glass column packed with SP-1240 DA on Supelcoport. Recoveries ranged from 86.6 + or - 9.1% (mean + or - SD) to 105 + or - 10.4%. Sensitivities for dichlorobenzenes and dichlorotoluenes were 8 ng/g for fat, 2 ng/g for tissue, and 0.4 ng/ml for blood.
Computed Properties
Molecular Weight:161.03
XLogP3:3.2
Rotatable Bond Count:1
Exact Mass:159.9846556
Monoisotopic Mass:159.9846556
Heavy Atom Count:9
Complexity:75
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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