ContaminantDB: Dibromochloromethane

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:22 UTC

Update Date

2026-03-27 00:49:41 UTC

Accession Number

CHEM000218

Identification

Common Name

Dibromochloromethane

Class

Small Molecule

Description

Dibromochloromethane (and bromoform also known as tribromomethane) are colorless to yellow, heavy, nonburnable liquids with a sweetish odor. These chemicals are possible contaminants of drinking water that has been chlorinated. Bromoform and dibromochloromethane may form when chlorine reacts with other naturally occurring substances in water, such as decomposing plant material. Plants in the ocean also produce small amounts of these chemicals. Carcinogenic effects have been observed in animals exposed to bromoform and dibromochloromethane. Dibromochloromethane induced liver tumors in male and female mice. The primary targets of bromoform and dibromochloromethane toxicit are liver, kidney, and central nervous system.

Contaminant Sources

Clean Air Act Chemicals
Disinfection Byproducts
HPV EPA Chemicals
IARC Carcinogens Group 3
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Bromide Compound
Food Toxin
Indicator and Reagent
Industrial/Workplace Toxin
Metabolite
Organic Compound
Organobromide
Organochloride
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Chlorodibromomethane	HMDB
Dibromo(chloro)methane	HMDB
Dibromo-chloro-methane	HMDB
Dibromochloromethane	KEGG

Chemical Formula

CHBr₂Cl

Average Molecular Mass

208.280 g/mol

Monoisotopic Mass

205.813 g/mol

CAS Registry Number

124-48-1

IUPAC Name

dibromo(chloro)methane

Traditional Name

dibromochloromethane

SMILES

ClC(Br)Br

InChI Identifier

InChI=1S/CHBr2Cl/c2-1(3)4/h1H

InChI Key

GATVIKZLVQHOMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Alkyl halides

Sub Class

Halomethanes

Direct Parent

Trihalomethanes

Alternative Parents

Substituents

Trihalomethane
Hydrocarbon derivative
Organochloride
Organobromide
Alkyl chloride
Alkyl bromide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine compound (CHEBI:34627 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless to pale yellow liquid. (17)

Experimental Properties

Property	Value
Melting Point	-20°C
Boiling Point	120 °C
Solubility	2.7 mg/mL at 20 °C [HEIKES,DL (1987)]

Predicted Properties

Property	Value	Source
Water Solubility	4.76 g/L	ALOGPS
logP	2.17	ALOGPS
logP	2.13	ChemAxon
logS	-1.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	26.98 m³·mol⁻¹	ChemAxon
Polarizability	10.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-0a5bd838330dc26d5a35	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-0a5bd838330dc26d5a35	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adi-0960000000-88b94675ee64d5a1fa39	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-331858b80ef37cc92b57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-331858b80ef37cc92b57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0090000000-331858b80ef37cc92b57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-23f04d542b2a35b2e302	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-23f04d542b2a35b2e302	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0090000000-23f04d542b2a35b2e302	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-262798c8821c1a784f9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-262798c8821c1a784f9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-0900000000-30e20910a1b4ef59649f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-1cd0365290e6754179c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-1cd0365290e6754179c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0090000000-1cd0365290e6754179c7	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-3900000000-2bd815439d7061bd9aa2	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (17) ; inhalation (17) ; dermal (17)

Mechanism of Toxicity

Dibromochloromethane is oxidized into trihalomethanol by the cytochrome P-450 mixed function oxidase system of liver. Trihalomethanol then decomposes by loss of hydrogen and halide ions to yield the dihalocarbonyl (an analogue of phosgene), which is a highly reactive molecule, and may undergo a number of reactions, including direct reaction with cellular nucleophiles to yield covalent adducts, reaction with two moles of glutathione (GSH) to yield CO and oxidized glutathione (GSSG), and hydrolysis to yield CO2. The fraction of the dose converted to carbon monoxide has not been quantified, but dramatically increased levels of carboxyhemoglobin have been reported following oral exposure of rats to bromoform. (17)

Metabolism

In humans and laboratory animals, dibromochloromethane (and bromoform) are generally absorbed quickly. Dibromochloromethane (and bromoform) are thought to be metabolized by at least two route-independent pathways: oxidation by cytochrome P-450 mixed function oxidase system and conjugation via glutathione S-transferase. After ingestion, excretion occurs primarily by exhalation of the compound or of CO2. (17)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (16)

Uses/Sources

Dibromochloromethane exposition occurs by drinking water that has been treated with chlorine, at a swimming pool, by breathing bromoform or dibromochloromethane that has evaporated into the air, or by uptake from the water through the skin. Neither dibromochloromethane nor bromoform are likely to be found in food. (17)

Minimum Risk Level

Not Available

Health Effects

Exposure to dibromochloromethane leads to central nervous system depression, which is probably the chief cause of death in acute exposures. Some studies in animals indicate that exposure to high doses of dibromochloromethane may also lead to liver and the kidney injury within a short period of time. (17)

Symptoms

Not Available

Treatment

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0059903

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID