Vinyl bromide (CHEM001555)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:38 UTC
Update Date2026-03-26 21:53:56 UTC
Accession NumberCHEM001555
Identification
Common NameVinyl bromide
ClassSmall Molecule
DescriptionVinyl bromide is an organobromide compound. It is used to manufacture bromopolymers, mainly polyvinyl bromide, and is also an alkylation agent. Vinyl bromide is primarily used in the manufacture of flame retardant synthetic fibers. Its copolymer with vinyl chloride is also used for preparing films, for laminating fibers, and as rubber substitutes. Vinyl bromide is highly flammable liquid and reacts violently with oxidizers.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2A
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-BromoethyleneChEBI
BromoethyleneChEBI
Bromure de vinyleChEBI
C2H3BRChEBI
MonobromoethyleneChEBI
VinylbromidChEBI
Chemical FormulaC2H3Br
Average Molecular Mass106.949 g/mol
Monoisotopic Mass105.942 g/mol
CAS Registry Number593-60-2
IUPAC Namebromoethene
Traditional Namevinyl bromide
SMILESBrC=C
InChI IdentifierInChI=1S/C2H3Br/c1-2-3/h2H,1H2
InChI KeyINLLPKCGLOXCIV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as vinyl bromides. These are vinyl halides in which a bromine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl bromides
Direct ParentVinyl bromides
Alternative Parents
Substituents
  • Bromoalkene
  • Haloalkene
  • Vinyl bromide
  • Hydrocarbon derivative
  • Organobromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateGas
AppearanceColorless gas.
Experimental Properties
PropertyValue
Melting Point-137.8°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.12 g/LALOGPS
logP1.19ALOGPS
logP1.59ChemAxon
logS-1.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity17.6 m³·mol⁻¹ChemAxon
Polarizability6.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2d4850396cc0c60e64edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-2d4850396cc0c60e64edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-ce568db8763478a2ac12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-f08d0ab13ddb4375450aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-e73387a14cfbcb27ab2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2900000000-59c012e017155a091443Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-6900000000-ca5d943e9f412373546aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityOrganobromide compounds, especially alkylbromides are strong alkylating agents. Consequently they can randomly modify the surfaces of proteins and lipids, leading to the disruption of enzyme, transporter or membrane functions. Alkylation of DNA by alkylbromides may also lead to mutations. Vinyl bromide is metabolically activated by liver microsomal enzymes to intermediates that covalently bind to proteins and nucleic acids. Several lines of evidence suggest the involvement of the epoxides, i.e., bromoethylene oxide. Proven targets for alkylation are adenine, cytosine and guanine moieties in nucleic acids, and sulfhydryl groups of proteins. Vinylbromide reacts quickly with hepatic glutathione (GSH) leading to its rapid depletion and subsequent liver damage.
MetabolismBromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (3)
Toxicity ValuesLD50: 500 mg/kg (Oral, Rat) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (2)
Uses/SourcesVinyl bromide is primarily used in the manufacture of flame retardant synthetic fibers. Workers may be occupationally exposed to vinyl bromide via inhalation during its manufacture or use.
Minimum Risk LevelNot Available
Health EffectsAcute (short-term) and chronic (long-term) studies indicate that the liver is the primary target organ following inhalation exposure to vinyl bromide in humans and animals. Acute exposure of rats to very high concentrations via inhalation has resulted in liver and kidney damage and adverse neurological effects. Chronic inhalation exposure primarily damages the liver, causing foci in the liver of rats. Vinyl bromide has been shown to be a potent carcinogen in rats exposed by inhalation, producing liver angiosarcomas.
SymptomsIn high concentrations, vinyl bromide may produce dizziness, disorientation, and sleepiness in humans.
TreatmentEYES: 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
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVinyl bromide
Chemspider IDNot Available
ChEBI ID51311
PubChem Compound ID11641
Kegg Compound IDC19184
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available