Record Information
Version2.0
Creation Date2009-06-22 16:08:38 UTC
Update Date2014-12-24 20:24:40 UTC
Accession NumberT3D1806
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.
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1-Bromoethylene
Bromoethene
Bromoethene (9CI)
Bromoethylene
Bromoethylene polymer
Bromure de vinyle
C2H3Br
Ethene, bromo-, homopolymer
Ethene, bromo-, homopolymer (9CI)
Ethylene, bromo-, polymer
Monobromoethylene
Polybromoethylene
Polyvinyl bromide
Polyvinylbromide
PVBR
Saytex VBR
Vinyl bromide polymer
Vinyl bromide solution
Vinyl bromide, inhibited
Vinyl-13C2 Bromide (gas)
Vinylbromid
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 KeyInChIKey=INLLPKCGLOXCIV-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
LogPNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2d4850396cc0c60e64ed2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-2d4850396cc0c60e64ed2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-ce568db8763478a2ac122016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-f08d0ab13ddb4375450a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-e73387a14cfbcb27ab2f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2900000000-59c012e017155a0914432016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-6900000000-ca5d943e9f412373546a2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6) ; dermal (6)
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. (6)
Toxicity ValuesLD50: 500 mg/kg (Oral, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (4)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID11641
ChEMBL IDNot Available
ChemSpider ID11151
KEGG IDC19184
UniProt IDNot Available
OMIM ID
ChEBI ID51311
BioCyc ID11-DCE
CTD IDC003763
Stitch IDVinyl bromide
PDB IDNot Available
ACToR ID1464
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1806.pdf
General References
  1. Bolt HM, Filser JG, Laib RJ, Ottenwalder H: Binding kinetics of vinyl chloride and vinyl bromide at very low doses. Arch Toxicol Suppl. 1980;3:129-42. [6930940 ]
  2. American Conference of Governmental Industrial Hygienists, Inc. (1991). Documentation of the Threshold Limit Values and Biological Exposure Indices. 6th ed. Volumes I, II, III. Cincinnati, OH: American Conference of Governmental Industrial Hygienists.
  3. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  5. Wikipedia. Vinyl bromide. Last Updated 24 March 2009. [Link]
  6. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Bolt HM, Filser JG, Laib RJ, Ottenwalder H: Binding kinetics of vinyl chloride and vinyl bromide at very low doses. Arch Toxicol Suppl. 1980;3:129-42. [6930940 ]
  2. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  3. Wikipedia. Vinyl bromide. Last Updated 24 March 2009. [Link]
References
  1. Bolt HM, Filser JG, Laib RJ, Ottenwalder H: Binding kinetics of vinyl chloride and vinyl bromide at very low doses. Arch Toxicol Suppl. 1980;3:129-42. [6930940 ]
  2. IARC (1983). Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-Present. (Multivolume work).
  3. Wikipedia. Vinyl bromide. Last Updated 24 March 2009. [Link]