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Home > Encyclopedia > Bromotrichloromethane

Bromotrichloromethane

Bromotrichloromethane structure

Bromotrichloromethane 

structure
  • CAS No:

    75-62-7

  • Formula:

    CBrCl3

  • Chemical Name:

    Bromotrichloromethane

  • Synonyms:

    Methane,bromotrichloro-;Bromotrichloromethane;Trichlorobromomethane;Carbon bromotrichloride;Monobromotrichloromethane;Trichloromethyl bromide;Carbon trichlorobromide;Carbon bromide trichloride (CBrCl3);Bromotrichlormethane;NSC 8017

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Clear colourless to slightly yellow liquid


A potent liver poison. In rats, bromotrichloromethane produces about three times the degree of liver microsomal lipid peroxidation as does carbon tetrachloride.

Bromotrichloromethane Basic Attributes

198.265

198.27

200-886-0

IKJ30QXM63

8017

DTXSID7023930

COLORLESS HEAVY LIQUID

29034700

Characteristics

0

2.70900

Colorless heavy liquid. Chloroform-like odor.

2.012 g/cm3 @ Temp: 25 °C

-5.7 °C

105 °C

104-105°C

n20/D 1.5065(lit.)

H2O: insoluble ;Very soluble in ether and ethanol

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

38.4 mm Hg ( 25 °C)

6.85 (vs air)

CHLOROFORM-LIKE ODOR

3.77X10+7 J/kmol @ -21 °C

Critical temperature: 333 °C; critical pressure: 49 atm

Safety Information

III

6.1

UN 2810 6.1/PG 2

3

R20/21/22;R36/37/38

S36/37-S36/37/39-S26

PA5400000

Xn:Harmful;

Stable at room temperature in closed containers under normal storage and handling conditions.

P280

H302 + H312 + H332

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.

DURING UNCATALYZED ADDITION OF BROMOTRICHLOROMETHANE TO ETHYLENE VIOLENT EXPLOSION OCCURRED.

|Warning|H302 (99.25%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 133 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

HEPATOCYTES FROM LIVERS OF RATS FED A SEMISYNTHETIC VITAMIN E-SUPPLEMENTED DIET WERE SLIGHTLY MORE PROTECTED FROM PEROXIDATION AND CELLULAR DAMAGE INDUCED BY BROMOTRICHLOROMETHANE TREATMENT THAN WERE HEPATOCYTES FROM RATS FED A VITAMIN E-DEFICIENT DIET.|WHEN INCUBATED FOR 15 MIN IN AIR WITH RAT LIVER MICROSOMES FROM PHENOBARBITAL-TREATED RATS, A NADPH-GENERATING SYSTEM, AND GSH (5 MILLIMOLAR), BROMOTRICHLOROMETHANE WAS CONVERTED TO DIGLUTATHIONYL DITHIOCARBONATE.|WHEN ISOLATED RAT HEPATOCYTES WERE INCUBATED WITH 2 MILLIMOLAR BROMOTRICHLOROMETHANE, INCR IN THE NUMBER OF CELLS TAKING UP TRYPAN BLUE, RELEASING LACTATE DEHYDROGENASE OR FORMING MALONDIALDEHYDE WAS OFFSET BY ADDING 1X10-4 MOLAR 2-HYDROXYESTRADIOL OR (+)-CYANIDANOL-3.|PROTECTIVE EFFECTS OF CADMIUM ACETATE IN TRICHLOROBROMOMETHANE POISONING.|For more Interactions (Complete) data for BROMOTRICHLOROMETHANE (6 total), please visit the HSDB record page.

LD50 Rat ip 119 mg/kg

Bromotrichloromethane has been identified as a volatile compound in both bacon(1) and pork(2).

Bromotrichloromethane's production and use in organic syntheses(1) may result in its release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 567(SRC), determined from an estimated log Kow(2,SRC) and a regression-derived equation(3), indicates that bromotrichloromethane is expected to have low mobility in soil(SRC). Volatilization of bromotrichloromethane from moist soil surfaces is expected (SRC) given an estimated Henry's Law constant of 3.7X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of bromotrichloromethane from dry soil surfaces may exist(SRC) based on a measured vapor pressure of 39 mm Hg(5). Based upon the highly halogenated structure of bromotrichloromethane, biodegradation in soil is expected to be slow(6,SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 567(SRC), determined from an estimated log Kow of 2.5(2,SRC) and a regression-derived equation(3), indicates that bromotrichloromethane is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.7X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.7 hrs and 6.6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 49(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate. Based upon the highly halogenated structure of bromotrichloromethane, biodegradation in water is expected to be slow(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromotrichloromethane, which has a measured vapor pressure of 39 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Based on bromotrichloromethane's structural similarity to bromotrifluoromethane, it is expected to slowly degrade in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for bromotrichloromethane's reaction in air is estimated to be greater than 44 years(3), based on bromotrifluoromethane's rate constant of <5.0X10-16 cu cm/molecule-sec at 25 °C(3). Photolysis may occur based on bromotrichloromethane's structural similarity to other halogenated methane compounds but not at an environmentally important rate(4).

Based on bromotrichloromethane's structural similarity to bromotrifluoromethane, it is expected to slowly degrade in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC). The half-life for this reaction in air is estimated to be greater than 44 years(1), based on bromotrifluoromethane's rate constant of <5.0X10-16 cu cm/molecule-sec at 25 °C(1). Although there is no experimental evidence of bromotrichloromethane hydrolyzing in the ambient environment, similarly structured organic halide compounds are known to hydrolyze at an extremely slow rate (half-lives > 100 years)(2). Photolysis may occur based on bromotrichloromethane's structural similarity to other halogenated methane compounds but not at a significant rate(3).

An estimated BCF value of 49 was calculated for bromotrichloromethane(SRC), using an estimated log Kow of 2.5(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is moderate(SRC).

The Koc of bromotrichloromethane is estimated as approximately 567(SRC), using an estimated log Kow of 2.5(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bromotrichloromethane is expected to have low mobility in soil(SRC).

The Henry's Law constant for bromotrichloromethane is estimated as 3.7X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that bromotrichloromethane is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 3.7 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 6.6 days(2,SRC). Bromotrichloromethane's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is expected(SRC). The potential for volatilization of bromotrichloromethane from dry soil surfaces may exist(SRC) based on an measured vapor pressure of 39 mm Hg(3).

SURFACE WATER: Bromotrichloromethane was detected in the Lake Ontario basin of the Niagara River at an unspecified concentration(1). Bromotrichloromethane was detected in the Lower Niagara River and Lake Ontario in 1981 at concentrations of 0.007 ug/l and 0.005 ug/l, respectively(2).|DRINKING WATER: Bromotrichloromethane was identified in drinking water at an unspecified location and concentration(1). Chlorinated water samples taken from Turku, Finland between 1981-84 contained bromotrichloromethane at a concentration of 0.02 ug/l(2). Chlorinated water from the Turku distribution network contained bromotrichloromethane at levels ranging from 0.12 ug/l to 0.16 ug/l(2).

Bromotrichloromethane was identified as a volatile compound from bacon(1). Bromotrichloromethane was identified as a meat volatile from pork(2).

Trace amounts of bromotrichloromethane were identified in pasteurized milk(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,821 workers (273 of these are female) are potentially exposed to bromotrichloromethane in the US(1). However, production of bromotrichloromethane has since been banned in the United States and therefore occupational exposure would only occur when using bromotrichloromethnae for organic synthesis(2,SRC). The general population may be exposed to bromotrichloromethane via ingestion of food(3,4) and drinking water(5,6).

Drug Information

AFTER ORAL ADMIN OF BROMOTRICHLOROMETHANE TO RATS, FORMATION OF RADICAL CBRCL2 AND CCL3 BY LIVER METABOLISM MAY OCCUR.|UTILIZING THE SPIN-TRAPPING AGENT PHENYL-TERT-BUTYL NITRONE, A FREE RADICAL, CCL3, WAS DETECTED WHICH IS PRODUCED FROM CARBON TETRACHLORIDE OR BROMOTRICHLOROMETHANE DURING ENZYMIC OXIDATION OF NADPH BY RAT LIVER MICROSOMES.|THE FREE CHLOROFORM RADICAL, BISALLYL RADICAL, & BROMODICHLOROMETHANE RADICAL WERE DETECTED IN RAT LIVERS POISONED WITH BROMOTRICHLOROMETHANE.

Cardiac arrhythmia, possibly aggravated by elevated levels of catecholamines due to stress ... is suggested as the cause of these adverse responses, which may lead to death. /Fluorocarbons/

Toxic by ingestion and inhalation of fumes.

Bromotrichloromethane

Bromotrichloromethane Use and Manufacturing

Methods of Manufacturing

At 225-275 °C bromination of the /chloroform/ vapor yields bromochloromethanes: CCl3Br, CCl2Br2, CClBr3

Uses

Organic synthesis.

Methane, bromotrichloro-: ACTIVE

Computed Properties

Molecular Weight:198.27
XLogP3:2.9
Exact Mass:195.82490
Monoisotopic Mass:195.82490
Heavy Atom Count:5
Complexity:28.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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