ContaminantDB: 1,2-Dibromoethane

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:57 UTC

Update Date

2026-03-26 20:40:15 UTC

Accession Number

CHEM000031

Identification

Common Name

1,2-Dibromoethane

Class

Small Molecule

Description

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is the organobromine compound with the chemical formula (CH2Br)2. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a colorless liquid with a sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant. The effects on people of breathing high levels are not known, but animal studies with short-term exposures to high levels caused depression and collapse, indicating effects on the brain.

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2A
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Bromide Compound
Gasoline Additive/Component
Industrial/Workplace Toxin
Metabolite
Organic Compound
Organobromide
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
alpha,beta-Dibromoethane	ChEBI
alpha,Omega-dibromoethane	ChEBI
DBE	ChEBI
EDB	ChEBI
Ethylene bromide	ChEBI
Ethylene dibromide	ChEBI
Sym-dibromoethane	ChEBI
a,b-Dibromoethane	Generator
Α,β-dibromoethane	Generator
a,Omega-dibromoethane	Generator
Α,omega-dibromoethane	Generator
Bromide, ethylene	HMDB
Dibromide, ethylene	HMDB
Dibromides, ethylene	HMDB
Dowfume W 85	HMDB
Dowfume w85	HMDB
Ethylene dibromides	HMDB
1,2 Dibromoethane	HMDB
Sym dibromoethane	HMDB
Carboxylic acid	Generator
Carboxylic acid	Generator

Chemical Formula

C₂H₄Br₂

Average Molecular Mass

187.861 g/mol

Monoisotopic Mass

185.868 g/mol

CAS Registry Number

106-93-4

IUPAC Name

1,2-dibromoethane

Traditional Name

dibromoethane

SMILES

BrCCBr

InChI Identifier

InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2

InChI Key

PAAZPARNPHGIKF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organobromides. Organobromides are compounds containing a chemical bond between a carbon atom and a bromine atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Organobromides

Sub Class

Not Available

Direct Parent

Organobromides

Alternative Parents

Substituents

Hydrocarbon derivative
Organobromide
Alkyl halide
Alkyl bromide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

bromoalkane (CHEBI:28534 )
a bromide (12-DIBROMOETHANE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

fumigant

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	9.9°C
Boiling Point	Not Available
Solubility	3.91 mg/mL at 25 °C [HORVATH,AL et al. (1999)]

Predicted Properties

Property	Value	Source
Water Solubility	3.06 g/L	ALOGPS
logP	2.08	ALOGPS
logP	1.87	ChemAxon
logS	-1.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.62 m³·mol⁻¹	ChemAxon
Polarizability	10.74 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)	splash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-5900000000-0f8e5929b65c18ffe174	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-5900000000-0f8e5929b65c18ffe174	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-3900000000-703ca88896dc7f353fc6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-000i-0900000000-9059cc10a7a8eb687fac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-ee5e7d28ff43cd849c39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-2578b34097bd653c4d1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-51a6eb4c9e7aa0216f9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-541ce06a61a5a4e27f0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0900000000-c16dec5f28cf43cf1857	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a6r-7900000000-505389611033d5f531b3	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
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (2) ; inhalation (2) ; dermal (2)

Mechanism of Toxicity

The metabolite 2-bromoacetaldehyde produces liver damage by binding to cellular proteins. S-(2-bromoethyl)glutathione, another metabolite, exerts genotoxic and carcinogenic effects by binding to DNA. Antispermatogenic effects of 1,2-dibromoethanes metabolites may be caused by their covalent binding to thiol groups of nucleoproteins in nuclei of spermatozoa. Such adduct formation interferes with DNA, causing improper packing of the chromatin. (2)

Metabolism

1,2-Dibromoethane is rapidly absorbed by ingestion, inhalation, and dermal routes, then distributed mainly to the kidneys, liver, and spleen. It can be metabolized by either the cytochrome P-450 system or the glutathione S-transferase system. Many of the metabolites are toxic, and include 2-bromoacetaldehyde and S-(2-bromoethyl)glutathione. These metabolites may be further broken down and excreted in the urine. (2)

Toxicity Values

LD50: 108 mg/kg (Oral, Rat) (4) LD50: 300 mg/kg (Dermal, Rat) (4) LD50: 220 mg/kg (Intraperitoneal, Mouse) (4) LC50: 14 300 mg/m3 over 30 minutes (Inhalation, Rat) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2A, probably carcinogenic to humans. (3)

Uses/Sources

1,2-Dibromoethane was once widely used as an additive in leaded gasoline and a pesticide, however, today it's use is restricted to only certain pesticides (treatment of logs for termites and beetles, control of moths in beehives) and dye preparations. (2)

Minimum Risk Level

Not Available

Health Effects

Long term exposure can result in liver, kidney, and reproductive system damage. 1,2-Dibromoethane is also known to have adverse effects on the brain. (2)

Symptoms

Redness and inflammation, including skin blisters and mouth and stomach ulcers, can occur if large amounts of 1,2-dibromoethane are swallowed. Breathing high levels may cause depression and collapse. (2)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0060334

FooDB ID

Not Available

Phenol Explorer ID