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Record Information
Version2.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2014-12-24 20:24:37 UTC
Accession NumberT3D1778
Identification
Common NameBromoacetone
ClassSmall Molecule
DescriptionBromoacetone is an organobromide compound. It is a lachrymatory agent and was used in World War I as a chemical weapon (called BA by British and B-Stoff by Germans) and later as a riot control agent. Today it is considered obsolete (due to its toxicity) and is no longer in use for riot control purposes, but is a useful reagent in organic synthesis. Bromoacetone is prepared by combining bromine and acetone with a catalytic acid such as sulfuric acid. Bromoacetone has been shown to be a by-product of drinking water treatment using chlorine dioxide and chloramines in water high in bromide concentrations. Bromoacetone is found in the essential oil of a seaweed species (Asparagopsis taxiformis) that grows in the ocean around the Hawaiian Islands. Bromoacetone is structurally similar to chloroacetone. Both chemicals are irritants however, data suggest that bromoacetone is more toxic than chloroacetone. As a chemical warfare or riot control agent, bromoacetone is/was considered to be a rapid acting casualty producing agent capable of causing casualties within minutes of dissemination. Eye exposure to as little as 1 mg can cause pain and irritation. Inhalation of as little as 2-5 mg can cause coughing, nose and throat irritation and congestion. Inhalation of higher concentrations may lead to severe sore throat, nasal congestion and serious discomfort. Skin contact with as little as 2-30 mg can produce irritation, itching, swelling and general discomfort. Skin exposure to 50-100mg may lead to blisters.
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Ketone
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Plant Toxin
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
.alpha.-bromoacetone
1-Bromo-2-propanone
1-Bromoacetone
1-bromopropan-2-one
2-Propanone, 1-bromo- (9CI)
a-bromoacetone
Acetonyl bromide
Acetyl methyl bromide
Acetylmethyl bromide
Alpha-bromoacetone
B-stoff
BA
Ba (tear gas)
Bromo-2-propanone
Bromomethyl methyl ketone
CH3COCH2Br
Martonite
Monobromoacetone
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 KeyInChIKey=VQFAIAKCILWQPZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha-haloketones. These are organic compounds contaning a halogen atom attached to the alpha carbon atom relative to C=O group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen 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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.93 m3·mol-1ChemAxon
Polarizability9.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-114a46436aee264a8b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-a2150678a0ca075da426View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-987e85ff1d4396fd36eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ce48ba63222ee36539b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-26e58be85ad504008105View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-3900000000-575f1cffaa38fbc4b509View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-184b073e6f5ecf8f9fffView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6) ; dermal (6)
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.
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). (7)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID11715
ChEMBL IDCHEMBL1085947
ChemSpider ID11223
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID51845
BioCyc IDACETONE
CTD IDC018235
Stitch IDBromoacetone
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1778.pdf
General References
  1. Garner CE, Sumner SC, Davis JG, Burgess JP, Yueh Y, Demeter J, Zhan Q, Valentine J, Jeffcoat AR, Burka LT, Mathews JM: Metabolism and disposition of 1-bromopropane in rats and mice following inhalation or intravenous administration. Toxicol Appl Pharmacol. 2006 Aug 15;215(1):23-36. Epub 2006 Mar 2. [16513153 ]
  2. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  3. Marrs, Timothy T., Robert L. Maynard, and Frederick Sidell, eds. (2007). Chemical Warfare Agents: Toxicology and Treatment. 2nd edition. John Wiley & Sons. [ISBN: 978-0-470-01359-5]
  4. Wikipedia. Bromoacetone. Last Updated 20 March 2009. [Link]
  5. ACUTE EXPOSURE GUIDELINE LEVELS (AEGLs) BROMOACETONE (CAS Reg. No. 598-31-2) INTERIM [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

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. Garner CE, Sumner SC, Davis JG, Burgess JP, Yueh Y, Demeter J, Zhan Q, Valentine J, Jeffcoat AR, Burka LT, Mathews JM: Metabolism and disposition of 1-bromopropane in rats and mice following inhalation or intravenous administration. Toxicol Appl Pharmacol. 2006 Aug 15;215(1):23-36. Epub 2006 Mar 2. [16513153 ]
  2. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
  3. Wikipedia. Bromoacetone. Last Updated 20 March 2009. [Link]
  4. ACUTE EXPOSURE GUIDELINE LEVELS (AEGLs) BROMOACETONE (CAS Reg. No. 598-31-2) INTERIM [Link]