An official website of the United States government

Bromotrichloromethane

PubChem CID
6383
Structure
Bromotrichloromethane_small.png
Bromotrichloromethane_3D_Structure.png
Molecular Formula
Synonyms
  • BROMOTRICHLOROMETHANE
  • 75-62-7
  • Trichlorobromomethane
  • Methane, bromotrichloro-
  • bromo(trichloro)methane
Molecular Weight
198.27 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
A potent liver poison. In rats, bromotrichloromethane produces about three times the degree of liver microsomal lipid peroxidation as does carbon tetrachloride.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Bromotrichloromethane.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

bromo(trichloro)methane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/CBrCl3/c2-1(3,4)5
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

XNNQFQFUQLJSQT-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C(Cl)(Cl)(Cl)Br
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

CBrCl3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

75-62-7

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 NSC Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Bromotrichloromethane
  • Trichlorobromomethane

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
198.27 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
195.82490 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
195.82490 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
5
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
28.4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Colorless liquid; Insoluble in water; [HSDB]

3.2.2 Color / Form

COLORLESS HEAVY LIQUID
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 173

3.2.3 Odor

CHLOROFORM-LIKE ODOR
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 173

3.2.4 Boiling Point

105 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-205

3.2.5 Melting Point

-5.7 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-205

3.2.6 Solubility

INSOL IN WATER; SOL IN ALL PROP IN ALCOHOL & ETHER
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-373
MISCIBLE WITH MANY ORG LIQUIDS
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 173
Very soluble in ether and ethanol
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-205

3.2.7 Density

2.012 @ 25 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-205

3.2.8 Vapor Pressure

39.0 [mmHg]
39 mm Hg at 25 °C
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.

3.2.9 Decomposition

When heated to decomposition it emits very toxic fumes of /hydrogen chloride/ and /hydrogen bromide/.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 531

3.2.10 Viscosity

3.29X10-3 Pa.s @ -21 °C
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.

3.2.11 Heat of Vaporization

3.77X10+7 J/kmol @ -21 °C
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.

3.2.12 Surface Tension

4.24X10-2 N/m @ -21 °C
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.

3.2.13 Refractive Index

MAX ABSORPTION (ISOOCTANE): 240 NM (LOG E= 2.3); INDEX OF REFRACTION: 1.5065 @ 20 °C/D
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-373
Index of refraction = 1.5065 @ 20 °C/D
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-205

3.2.14 Kovats Retention Index

Standard non-polar
754 , 762 , 772 , 750 , 757 , 759 , 752.1
Standard polar
1075.59 , 1087.48 , 1101.23 , 1070

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Halogenated Aliphatics, Saturated

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 6
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

119 99.99

117 99.03

47 42.90

163 39.39

82 36.38

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 6
View All
NIST Number
228694
Library
Main library
Total Peaks
45
m/z Top Peak
117
m/z 2nd Highest
119
m/z 3rd Highest
163
Thumbnail
Thumbnail

4.2.2 Other MS

1 of 2
Other MS
MASS: 1364 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Other MS
MASS: 1116 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
2 of 2
Authors
NARA WOMEN'S UNIVERSITY
Instrument
HITACHI M-80
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

119 999

117 990

47 429

163 394

82 364

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 IR Spectra

IR Spectra
IR: 1845 (Sadtler Research Laboratories Prism Collection)

4.3.1 FTIR Spectra

1 of 2
Technique
NEAT
Source of Sample
Eastman Kodak Company, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bio-Rad FTS
Technique
Neat (KBr)
Source of Spectrum
Forensic Spectral Research
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
PerkinElmer SpectrumTwo
Technique
ATR-IR
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
ATR-Neat
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
B82251
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

AFTER ORAL ADMIN OF BROMOTRICHLOROMETHANE TO RATS, FORMATION OF RADICAL CBRCL2 AND CCL3 BY LIVER METABOLISM MAY OCCUR.
BINI A ET AL; PHARMACOL RES COMMUN 7 (2): 143 (1975)
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.
POYER JL ET AL; BIOCHIM BIOPHYS ACTA 539 (3): 402 (1978)
THE FREE CHLOROFORM RADICAL, BISALLYL RADICAL, & BROMODICHLOROMETHANE RADICAL WERE DETECTED IN RAT LIVERS POISONED WITH BROMOTRICHLOROMETHANE.
BINI A ET AL; RASS MED SARDA 78 (4): 347 (1975)

7.2 Mechanism of Action

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/
WHO; Environmental Health Criteria 113: Fully Halogenated Chlorofluorocarbons p.20 (1990)

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used in organic synthesis and as a flame retardant; [HSDB]
ORGANIC SYNTHESIS
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 173
FLAME RETARDANT
Addition /to isoprene/ is induced using bromotrichloromethane in a 3:1 mol ratio to isoprene by x-irradiation at 60 Gy/min. The main reaction yields a mixture of ca 75% 1,4 and 25% 4,1 addition product
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V14 (95) 940

8.2 Methods of Manufacturing

At 225-275 °C bromination of the /chloroform/ vapor yields bromochloromethanes: CCl3Br, CCl2Br2, CClBr3
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V5 696

8.3 General Manufacturing Information

EPA TSCA Commercial Activity Status
Methane, bromotrichloro-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (31.9%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (71.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (71.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (28.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 135 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (98.5%)

Acute Tox. 4 (31.9%)

Skin Irrit. 2 (71.9%)

Eye Irrit. 2A (71.9%)

Acute Tox. 4 (28.9%)

9.1.3 Hazards Summary

Intraperitoneal LD50 (rat) = 119 mg/kg; Causes CNS depression; [ChemIDplus] Causes liver injury in animal studies; [HSDB]

9.2 Safety and Hazard Properties

9.2.1 Critical Temperature & Pressure

Critical temperature: 333 °C; critical pressure: 49 atm
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.

9.3 Accidental Release Measures

9.3.1 Disposal Methods

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.

9.4 Stability and Reactivity

9.4.1 Hazardous Reactivities and Incompatibilities

DURING UNCATALYZED ADDITION OF BROMOTRICHLOROMETHANE TO ETHYLENE VIOLENT EXPLOSION OCCURRED.
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 491-37

9.5 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Methane, bromotrichloro-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Bromotrichloromethane: Does not have an individual approval but may be used under an appropriate group standard

10 Toxicity

10.1 Toxicological Information

10.1.1 EPA IRIS Information

Toxicity Summary
EPA IRIS Summary PDF (Update: Mar-01-1991 )

10.1.2 Evidence for Carcinogenicity

Cancer Classification: Group D Not Classifiable as to Human Carcinogenicity
USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch: "Chemicals Evaluated for Carcinogenic Potential" (April 2006)
CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Based on no data regarding the carcinogenicity of bromotrichloromethane in humans or animals. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: None.
U.S. Environmental Protection Agency's Integrated Risk Information System (IRIS). Summary on Bromotrichloromethane (75-62-7). Available from, as of March 15, 2000: https://www.epa.gov/iris/

10.1.3 Adverse Effects

Neurotoxin - Acute solvent syndrome

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

10.1.4 Acute Effects

10.1.5 Interactions

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.
GEE DL, TAPPEL AL; TOXICOL APPL PHARMACOL 60 (1): 112 (1981)
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.
POHL LR ET AL; DRUG METAB DISPOS 9 (4): 334 (1981)
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.
KAPPUS H ET AL; ARCH TOXICOL SUPPLEMENT 2: 321 (1979)
PROTECTIVE EFFECTS OF CADMIUM ACETATE IN TRICHLOROBROMOMETHANE POISONING.
DESSI A ET AL; BOLL SOC ITAL BIOL SPER 54 (17): 1659 (1978)
For more Interactions (Complete) data for BROMOTRICHLOROMETHANE (6 total), please visit the HSDB record page.

10.1.6 Human Toxicity Excerpts

Toxic by ingestion and inhalation of fumes.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 173

10.1.7 Non-Human Toxicity Excerpts

INHALATION OF BROMOTRICHLOROMETHANE BY RATS INCR AMT OF TOTAL LIPIDS IN LIVER & STIMULATED HEPATIC LIPID PEROXIDATION. AFTER INTRAGASTRIC ADMIN, LIVER CHANGES INCLUDED STEATOSIS, SWELLING OF ENDOPLASMIC RETICULUM, POLYSOME BREAKDOWN, DISAPPEARANCE OF GLUCOSE 6-PHOSPHATASE.
CALLIGARO A ET AL; SPERIMENTALE 121 (1): 1 (1971)
BROMOTRICHLOROMETHANE WAS MORE EFFICIENT THAN ETHANOL IN PROMOTING LIPID PEROXIDATION, AS INDICATED BY INCREASED AMOUNTS OF PEROXIDATION PRODUCTS IN BREATH OF ANIMALS.
FRANK H ET AL; APPL HEADSPACE GAS CHROMATOGR, (GC HEADSPACE SYMP) 155 (1980)
EFFECT OF BROMOTRICHLOROMETHANE METABOLISM ON CALCIUM PUMP OF FE(2+)-FREE RAT LIVER MICROSOMES WAS STUDIED. LIPID PEROXIDATION INDUCED BY BROMOTRICHLOROMETHANE-NADPH WAS ACCOMPANIED BY LEAKAGE OF CALCIUM FROM CALCIUM-LOADED MICROSOMES.
LOWREY K ET AL; BIOCHEM PHARMACOL 30 (2): 135 (1981)
RATS INJECTED WITH 0.26 MILLIMOLE BROMOTRICHLOROMETHANE DIED AFTER MASS ACCUM OF NEUTRAL LIPIDS IN AND NECROSIS OF THE LIVER. UNDER THE SAME CONDITIONS, THE LETHAL DOSE OF CARBON TETRACHLORIDE WAS 20-FOLD HIGHER THAN THAT OF BROMOTRICHLOROMETHANE.
BURDINO E ET AL; AGENTS ACTIONS 3 (4): 244 (1973)
For more Non-Human Toxicity Excerpts (Complete) data for BROMOTRICHLOROMETHANE (8 total), please visit the HSDB record page.

10.1.8 Non-Human Toxicity Values

LD50 Rat ip 119 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 531

10.2 Ecological Information

10.2.1 Environmental Fate / Exposure Summary

Although bromotrichloromethane is no longer produced in the United States, it is stil used in organic syntheses may result in its release to the environment. If released to the atmosphere, bromotrichloromethane is expected to exist solely as a vapor in the ambient atmosphere based on a measured vapor pressure of 39 mm Hg at 25 °C. Vapor-phase bromotrichloromethane is expected to degrade slowly in the atmosphere by reaction with photochemically-produced hydroxyl radicals based on its structural similarity to bromotrifluoromethane; the half-life for this reaction in air is estimated to be greater than 44 years. Photolysis may occur based on bromotrichloromethane's structural similarity to other halogenated methane compounds but not at an environmentally important rate. If released to soil, bromotrichloromethane is expected to have low mobility based on an estimated Koc of 567. The potential for volatilization of bromotrichloromethane from dry soil surfaces may exist based on this compound's vapor pressure. Bromotrichloromethane may volatilize from moist soil surfaces based on an estimated Henry's Law constant of 3.7X10-4 atm-cu m/mole at 25 °C. Volatilization from water surfaces is expected based on the estimated Henry's Law constant for this compound. Estimated volatilization half-lives from a model river and model lake are 7.4 hours and 6.6 days, respectively. An estimated BCF of 49 suggests the potential for bioconcentration in aquatic organisms is moderate. Based upon the highly halogenated structure of bromotrichloromethane, biodegradation in the environment is expected to be slow. Occupational exposure to bromotrichloromethane may occur through inhalation or dermal contact with this compound in workplaces where it is produced or used. The general population may be exposed to bromotrichloromethane via ingestion of food and drinking water. (SRC)

10.2.2 Natural Pollution Sources

Bromotrichloromethane has been identified as a volatile compound in both bacon(1) and pork(2).
(1) Ho CT et al; J Agric Food Chem 31: 336-42 (1983)
(2) Shahidi F et al; CRC Crit Rev Food Sci Nature 24: 141-243 (1986)

10.2.3 Artificial Pollution Sources

Bromotrichloromethane's production and use in organic syntheses(1) may result in its release to the environment(SRC).
(1) Lewis RJ Jr; Hawley's Condensed Chemical Dictionary 12th ed NY, NY: Van Nostrand Reinhold Co p. 173 (1993)

10.2.4 Environmental Fate

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).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 4-9 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng., NY, NY: Hemisphere Pub Corp, Vol 1 (1989)
(6) Boethling RS et al; Environ Sci Technol 28: 459-65 (1994)
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).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(7) Boethling RS et al; Environ Sci Technol 28: 459-65 (1994)
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).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng., NY, NY: Hemisphere Pub Corp, Vol 1 (1989)
(3) Atkinson R et al; Atmos Environ 26A: 1187-230 (1992)
(4) Orkin VL et al; J Atmos Chem 21: 1-11 (1995)

10.2.5 Environmental Biodegradation

Biodehalogenation of bromotrichloromethane by hydrogenolysis occurred in cultures with Pseudomonas putida(1). Based upon the highly halogenated structure of bromotrichloromethane, biodegradation is expected to be slow(2).
(1) Castro CE; Chemosphere 12: 1609-18 (1993)
(2) Boethling RS et al; Environ Sci Technol 28: 459-65 (1994)

10.2.6 Environmental Abiotic Degradation

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).
(1) Atkinson R et al; Atmos Environ 26A: 1187-230 (1992)
(2) Mabey W et al; J Phys Chem Ref Data Vol 7: 383-415 (1978)
(3) Orkin VL et al; J Atmos Chem 21: 1-11 (1995)

10.2.7 Environmental Bioconcentration

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).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Meylan WM et al; Env Toxic Chem 18: 664-672 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

10.2.8 Soil Adsorption / Mobility

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).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 23 (1983)

10.2.9 Volatilization from Water / Soil

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).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng., NY,NY: Hemisphere Pub Corp, Vol 1 (1989)

10.2.10 Environmental Water Concentrations

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).
(1) Great Lakes Water Quality Board, An Inventory of Chemical Substances Identified in the Great Lakes Ecosystem Vol 1 Summary, Report to the Great Lakes Water Quality Board, Windsor Ontario, Canada (1983)
(2) Strachan WMJ, Edwards CJ; Adv Environ Sci Technol 14: 239-64 (1984)
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).
(1) Kool HJ et al; Crit Rev Env Control 12: 307-57 (1982)
(2) Kroneld R; Bull Environ Contam Toxicol 37: 677-85 (1986)

10.2.11 Food Survey Values

Bromotrichloromethane was identified as a volatile compound from bacon(1). Bromotrichloromethane was identified as a meat volatile from pork(2).
(1) Ho CT et al; J Agric Food Chem 31: 336-42 (1983)
(2) Shahidi F et al; CRC Crit Rev Food Sci Nature 24: 141-243 (1986)

10.2.12 Milk Concentrations

Trace amounts of bromotrichloromethane were identified in pasteurized milk(1).
(1) Kroneld R, Reunanen M; Bull Environ Contam Toxicol 44: 917-23 (1990)

10.2.13 Probable Routes of Human Exposure

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).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)
(2) Lewis RJ Sr, ed; Hawley's Condensed Chemical Dictionary. 13th ed. NY, NY: John Wiley and Sons, Inc p. 167 (1997)
(3) Kroneld R, Reunanen M; Bull Environ Contam Toxicol 44: 917-23 (1990)
(4) Shahidi F et al; CRC Crit Rev Food Sci Nature 24: 141-243 (1986)
(5) Kool HJ et al; Crit Rev Env Control 12: 307-57 (1982)
(6) Kroneld R; Bull Environ Contam Toxicol 37: 677-85 (1986)

11 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Solvents, acute toxic effect [Category: Acute Poisoning]

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChemIDplus

15.3 UN GHS Classification

15.4 NORMAN Suspect List Exchange Classification

15.5 EPA DSSTox Classification

15.6 EPA TSCA and CDR Classification

15.7 EPA Substance Registry Services Tree

15.8 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. EPA Integrated Risk Information System (IRIS)
  8. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  9. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. Hazardous Substances Data Bank (HSDB)
  11. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  12. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  13. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  14. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  15. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
    Bromotrichloromethane
    https://haz-map.com/Agents/4010
  16. MassBank Europe
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  19. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Methane, bromotrichloro-
    http://www.nist.gov/srd/nist1a.cfm
  20. SpectraBase
  21. Springer Nature
  22. SpringerMaterials
  23. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  24. Wikidata
  25. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  26. PubChem
  27. GHS Classification (UNECE)
  28. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  29. EPA Substance Registry Services
  30. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  31. PATENTSCOPE (WIPO)
CONTENTS