Bromoacetic acid (CHEM001527)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2026-03-31 18:45:35 UTC
Accession NumberCHEM001527
Identification
Common NameBromoacetic acid
ClassSmall Molecule
DescriptionBromoacetic acid is an organobromide compound. It is an alkylating agent used primarily as a chemical intermediate in various organic syntheses. Bromoacetic acid and its esters are widely used building blocks in organic synthesis, for example in the pharmaceutical chemistry. Bromoacetic acid is also produced as a by-product through drinking water disinfection.
Contaminant Sources
  • Disinfection Byproducts
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
bromo-Acetic acidChEMBL
2-Bromoacetic acidChEMBL
bromo-AcetateGenerator
BromoacetateGenerator, MeSH
2-BromoacetateGenerator
MonobromoacetateMeSH
Chemical FormulaC2H3BrO2
Average Molecular Mass138.948 g/mol
Monoisotopic Mass137.932 g/mol
CAS Registry Number79-08-3
IUPAC Name2-bromoacetic acid
Traditional Nameto ntu
SMILESOC(=O)CBr
InChI IdentifierInChI=1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyKDPAWGWELVVRCH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAlpha-halocarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • 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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite to pale yellow crystals.
Experimental Properties
PropertyValue
Melting Point50°C
Boiling Point206 - 208°C
Solubility1750 mg/mL at 25°C [BOWDEN,DJ et al. (1998A)]
Predicted Properties
PropertyValueSource
Water Solubility107 g/LALOGPS
logP0.53ALOGPS
logP0.5ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)2.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.38 m³·mol⁻¹ChemAxon
Polarizability8.39 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-0900000000-0f29157733f334c58af7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-65083568b781ed35c83aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2900000000-5672959e96eba9a58497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-c49a481e327eca2f6d13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-b36c446c2f08c51169beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-bba1d1be8e1fc8a66b09Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-9100000000-2f67f020965bfe36eaffSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
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. 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. Alkylation of DNA by organobromides may also lead to mutations.
MetabolismNot Available
Toxicity ValuesLD50: 177 mg/kg (Oral, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBromoacetici acid is an industrial and laboratory chemical. It is produced as a drinking water disinfection by-product and small amounts may be found in treated drinking water.
Minimum Risk LevelNot Available
Health EffectsBromoacetic acid is a strong lachrymator. Animal studies have also indicated that bromoacetic acid is a teratogen (a developmental toxin) leading to soft tissue malformations in fetuses at doses of 100 mg/kg/day. Bromoacetic acid is also a mutagen and a cytotoxic agent.
SymptomsContact can lead to severe skin and eye burns, it can also irritate the nose throat and lungs if inhaled. Inhalation may result in spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin.
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 IDDB02198
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 LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6227
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available