Allyl bromide (CHEM001524)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2026-03-31 17:07:28 UTC
Accession NumberCHEM001524
Identification
Common NameAllyl bromide
ClassSmall Molecule
DescriptionAllyl bromide (3-bromopropene) is an alkyl bromide. It is primarily used as a starting material/chemical intermediate in organic synthesis and as an intermediate in the manufacture of polymers/resins, synthetic perfumes, pharmaceuticals, agricultural chemicals, and other allyl compounds. It has been described as an insecticidal fumigant used in crop protection. Physically, allyl bromide is a clear liquid with an intense, acrid, and persistent smell. It is highly flammable.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC3H5Br
Average Molecular Mass120.976 g/mol
Monoisotopic Mass119.957 g/mol
CAS Registry Number106-95-6
IUPAC Name3-bromoprop-1-ene
Traditional Nameallyl bromide
SMILESBrCC=C
InChI IdentifierInChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2
InChI KeyBHELZAPQIKSEDF-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.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganobromides
Sub ClassNot Available
Direct ParentOrganobromides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organobromide
  • Alkyl halide
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-119°C
Boiling Point71°C
Solubility3.83 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility1.84 g/LALOGPS
logP1.98ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability8.72 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, Positivesplash10-00di-0900000000-dc2798bc4320ac00ce3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-90605e0938aa899b636dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-6900000000-dc663ff811e7029a0f11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-972c849a92814a3a54f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-4900000000-1e620dd294c28a3bd6c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9100000000-a305c2f80f5b8f32b2f5Spectrum
MSMass Spectrum (Electron Ionization)splash10-000f-9100000000-4b666c62378e1d2fd21bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityOrganobromide compounds such as allylbromide are strong alkylating agents. Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. Allyl bromide appears to target the stomach and lining of the stomach as animals given chronically high doses exhibit lesions of the forestomach, including hyperplasia, inflammation, degeneration, and hyperkeratosis. Alkylation of DNA by alkylbromides may also lead to mutations or a reduced ability of cells to divide.
MetabolismAllyl bromide is metabolized into allylmercapturic acid, S-allylcysteine, and S-allylcysteine S-oxide and secreted in the urine. 3-Hydroxypropylmercapturic acid is also a metabolite.
Toxicity ValuesLD50: 30 mg/kg (Oral, Guinea pig) (6) LD50: 108 mg/kg (Intraperitoneal, Mouse) (6) LC50: 10 000 mg/kg (Inhalation, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (3)
Uses/SourcesAllyl bromide is an industrial and laboratory chemical. Occupational exposure to Allyl bromide may occur through inhalation and dermal contact with this compound at workplaces where Allyl bromide is produced or used.
Minimum Risk LevelNot Available
Health EffectsAcute poisoning of laboratory animals is accompanied by a transient motor agitation followed by depression and loss of balance. Death occurs within 24 hours. Allyl bromide is considered as one of the most toxic of the halogenated hydrocarbons, causing deaths in experimental animals exposed for 4 hr to concentrations as low as 1 mg/L. It is mutagenic but there is no evidence that it is carcinogenic. Target organs are gastrointestinal system, eyes, skin, respiratory system.
SymptomsCauses severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Causes gastrointestinal burns.
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 LinkAllyl bromide
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID7841
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available