Bromoacetone (CHEM001528)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (26)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2026-08-22 12:58:17 UTC
Accession NumberCHEM001528
Identification
Common NameBromoacetone
ClassSmall Molecule
DescriptionBromoacetone (C3H5BrO) is an exogenous liquid with an average molecular weight of 136.97 g/mol. Bromoacetone belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. Biologically, it functions as a lachrymator and targets the transient receptor potential cation channel subfamily A member 1 (TRPA1). The compound is found in or released from seven recorded sources, including food contact materials, soap detergents and perfumes within detergents, and electrical and electronic equipment such as hybrid capacitors, television systems, electrodes, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for bromoacetone include oral, touch, and inhalation.
Contaminant Sources
  • Clean Air Act Chemicals
  • T3DB toxins
Contaminant Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Ketone
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Plant Toxin
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Bromo-2-propanoneChEBI
Acetonyl bromideChEBI
alpha-BromoacetoneChEBI
Bromomethyl methyl ketoneChEBI
MonobromoacetoneChEBI
a-BromoacetoneGenerator
Α-bromoacetoneGenerator
Chemical FormulaC3H5BrO
Average Molecular Mass136.975 g/mol
Monoisotopic Mass135.952 g/mol
CAS Registry Number598-31-2
IUPAC Name1-bromopropan-2-one
Traditional Namebromoacetone
SMILESCC(=O)CBr
InChI IdentifierInChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3
InChI KeyVQFAIAKCILWQPZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-haloketones. These are organic compounds contaning a halogen atom attached to the alpha carbon atom relative to C=O group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-haloketones
Alternative Parents
Substituents
  • Alpha-haloketone
  • Organic oxide
  • Hydrocarbon derivative
  • Organobromide
  • Organohalogen compound
  • Alkyl halide
  • Alkyl bromide
  • 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 Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid, with a pungent odour. Commercial product is yellow-brown.
Experimental Properties
PropertyValue
Melting Point-36.5°C
Boiling Point137°C
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.9 g/LALOGPS
logP0.38ALOGPS
logP0.83ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)17.8ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.93 m³·mol⁻¹ChemAxon
Polarizability9.44 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, Positivesplash10-000i-0900000000-114a46436aee264a8b5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-a2150678a0ca075da426Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-987e85ff1d4396fd36eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ce48ba63222ee36539b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-26e58be85ad504008105Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-3900000000-575f1cffaa38fbc4b509Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-184b073e6f5ecf8f9fffSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityOrganobromide compounds such as bromoacetone 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. Very effecitve lachrymator at 1.5 mg/m3.
MetabolismBromoacetone is a metabolic byproduct of bromopropane. It can react with glutathione and generate conjugates that are subsequently secreted in the urine.
Toxicity ValuesVery effecitve lachrymator at 1.5 mg/m3.
Lethal DoseLethal at 3.2 mg/m3 for 10 min.
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (2)
Uses/SourcesBromoacetone is an industrial and laboratory chemical. Occupational exposure to bromoacetone may occur through inhalation and dermal contact with this compound at workplaces where bromoacetone is produced or used.
Minimum Risk LevelNot Available
Health EffectsA strong lachrymator. Inhalation, ingestion or skin contact with material may cause severe injury or death. Animal studies indicate that at very high concentrations it can cause kidney and liver damage. Bromoacetone causes ocular irritation in 30% of human subjects at 0.1 ppm and 100% of human subjects at 1.0 ppm.
SymptomsBromoacetone is a strong lachrymator. Inhalation leads to a burning sensation, cough, sore throat, labored breathing. Skin exposure causes redness, pain. Eyes exposure causes watering of the eyes, redness, pain, blurred vision. Ingestion leads to abdominal pain, burning sensation in the throat and chest, cough, diarrhea, nausea, vomiting.
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 LinkBromoacetone
Chemspider IDNot Available
ChEBI ID51845
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available