Allyl bromide (T3D1774)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2014-12-24 20:24:37 UTC
Accession NumberT3D1774
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.
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Bromo-2-propene
2-Propenyl bromide
3-Bromo-1-propene
3-bromoprop-1-ene
3-Bromopropene
3-Bromopropylene
Bromallylene
CH2=CHCH2Br
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 KeyInChIKey=BHELZAPQIKSEDF-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)]
LogPNot Available
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-dc2798bc4320ac00ce3a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-90605e0938aa899b636d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-6900000000-dc663ff811e7029a0f112016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-972c849a92814a3a54f12016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-4900000000-1e620dd294c28a3bd6c32016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9100000000-a305c2f80f5b8f32b2f52016-08-04View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000f-9100000000-4b666c62378e1d2fd21b2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6) ; dermal (6)
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) (3) LD50: 108 mg/kg (Intraperitoneal, Mouse) (3) LC50: 10 000 mg/kg (Inhalation, Rat) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (7)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID7841
ChEMBL IDCHEMBL1429506
ChemSpider ID7553
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDPROPENE
CTD IDC050431
Stitch IDAllyl bromide
PDB IDNot Available
ACToR ID7068
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1774.pdf
General References
  1. Toxicology studies of allyl bromide (CAS No. 106-95-6) in genetically modified (FVB Tg.AC hemizygous) mice and carcinogenicity studies of allyl bromide in genetically modified [B6.129-Trp53tm1Brd (N5) Haploinsufficient] mice (dermal and gavage studies). Natl Toxicol Program Genet Modif Model Rep. 2008 Apr;(7):1-122. [18784760 ]
  2. Lijinsky W, Andrews AW: Mutagenicity of vinyl compounds in Salmonella typhimurium. Teratog Carcinog Mutagen. 1980;1(3):259-67. [6119816 ]
  3. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  4. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  5. Wikipedia. Allyl bromide. Last Updated 12 March 2009. [Link]
  6. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  7. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [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. Lijinsky W, Andrews AW: Mutagenicity of vinyl compounds in Salmonella typhimurium. Teratog Carcinog Mutagen. 1980;1(3):259-67. [6119816 ]
  2. Toxicology studies of allyl bromide (CAS No. 106-95-6) in genetically modified (FVB Tg.AC hemizygous) mice and carcinogenicity studies of allyl bromide in genetically modified [B6.129-Trp53tm1Brd (N5) Haploinsufficient] mice (dermal and gavage studies). Natl Toxicol Program Genet Modif Model Rep. 2008 Apr;(7):1-122. [18784760 ]
  3. Wikipedia. Allyl bromide. Last Updated 12 March 2009. [Link]
Target Details
2. Glutathione
References
  1. Lijinsky W, Andrews AW: Mutagenicity of vinyl compounds in Salmonella typhimurium. Teratog Carcinog Mutagen. 1980;1(3):259-67. [6119816 ]
  2. Toxicology studies of allyl bromide (CAS No. 106-95-6) in genetically modified (FVB Tg.AC hemizygous) mice and carcinogenicity studies of allyl bromide in genetically modified [B6.129-Trp53tm1Brd (N5) Haploinsufficient] mice (dermal and gavage studies). Natl Toxicol Program Genet Modif Model Rep. 2008 Apr;(7):1-122. [18784760 ]
  3. Wikipedia. Allyl bromide. Last Updated 12 March 2009. [Link]
Target Details
3. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Lijinsky W, Andrews AW: Mutagenicity of vinyl compounds in Salmonella typhimurium. Teratog Carcinog Mutagen. 1980;1(3):259-67. [6119816 ]
  2. Toxicology studies of allyl bromide (CAS No. 106-95-6) in genetically modified (FVB Tg.AC hemizygous) mice and carcinogenicity studies of allyl bromide in genetically modified [B6.129-Trp53tm1Brd (N5) Haploinsufficient] mice (dermal and gavage studies). Natl Toxicol Program Genet Modif Model Rep. 2008 Apr;(7):1-122. [18784760 ]
  3. Wikipedia. Allyl bromide. Last Updated 12 March 2009. [Link]