1-Chloro-4-(chloromethyl)benzene

Log Kow = 3.18

3.18

COLORLESS LIQUID

Colorless needles

SOL IN CARBON DISULFIDE; SLIGHTLY SOL IN ALCOHOL

>10% in benzene

>10% in ethyl ether

>10% in acetic acid

For more Solubility (Complete) data for 1-CHLORO-4-CHLOROMETHYLBENZENE (7 total), please visit the HSDB record page.

Danger

H302+H312+H332 (87.5%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P333+P317, P337+P317, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 96 reports by 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]

Chemical: Benzene, 1-chloro-4-(chloromethyl)-

Status: Active Update: 04-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5414

4-Chlorobenzyl chloride: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

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.

/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.

para-Chlorobenzyl chloride, liquid or solid

Marine pollutant

Acute Tox. 4 (96.9%)

Acute toxicity (Oral) - Category 4

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.

UN 2235; Chlorobenzyl chlorides

IMO 6.1; Chlorobenzyl chlorides

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/

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.

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.

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 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.

1-Chloro-4-chloromethylbenzene was dehalogenated by a resting cell suspension of a soil bacterium, a Pseudomonas, that was isolated because of its ability to grow on 1,9-dichlorononane, although the bacterium was not able to grow on 1-chloro-4-chloromethylbenzene(1). Products formed after 24 hr of incubation were p-chlorobenzyl alcohol and p-chlorobenzoic acid(1). The p-chlorobenzyl alcohol was also formed in controls and therefore was produced, at least partially, by chemical hydrolysis(1). 1-Chloro-4-chloromethylbenzene is reported to degrade in a biodegradability screening test utilizing an activated sludge inoculum after 5 to 10 days incubation(2).

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 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).

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).

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).

1-Chloro-4-chloromethylbenzene's use as an intermediate for organic chemicals, pharmaceuticals, and dyes may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.9 mm Hg at 25 °C indicates 1-chloro-4-chloromethylbenzene will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chloro-4-chloromethylbenzene will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 13 days. 1-Chloro-4-chloromethylbenzene has an adsorption band at 275 nm that extends to about 295 nm, suggesting 1-chloro-4-chloromethylbenzene may potentially undergo direct photolysis. If released to soil, 1-chloro-4-chloromethylbenzene is expected to have low mobility based upon an estimated Koc of 1,300. Volatilization from moist soil surfaces may be an important fate process based upon an estimated Henry's Law constant of 3.4X10-4 atm-cu m/mole. However, hydrolysis may attenuate volatilization from moist soil surfaces. 1-Chloro-4-chloromethylbenzene may potentially volatilize from dry soil surfaces based upon its vapor pressure. However, volatilization from soil surfaces is expected to be attenuated by adsorption to soil. If released into water, 1-chloro-4-chloromethylbenzene is expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces may be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 7.0 hours and 6.0 days, respectively. Adsorption to suspended solids and sediment in the water column is expected to attenuate volatilization. Hydrolysis is expected to be an important process in aquatic systems and moist soils, based upon an estimated hydrolysis half-life of 25.5 hours at 25 °C. An estimated BCF of 150 suggests the potential for bioconcentration in aquatic organisms is high. However, bioconcentration in aquatic organisms may be attenuated by hydrolysis. 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)

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.

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.