<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">1781</id>
  <title>T3D1777</title>
  <common-name>Bromoacetic acid</common-name>
  <description>Bromoacetic 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.</description>
  <cas>79-08-3</cas>
  <pubchem-id>6227</pubchem-id>
  <chemical-formula>C2H3BrO2</chemical-formula>
  <weight>137.931640</weight>
  <appearance>White to pale yellow crystals.</appearance>
  <melting-point>50°C</melting-point>
  <boiling-point>206 - 208°C</boiling-point>
  <density nil="true"/>
  <solubility>1750 mg/mL at 25°C [BOWDEN,DJ et al. (1998A)]</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L626) ; inhalation (L626) ; dermal (L626)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Organobromide 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.</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity>LD50: 177 mg/kg (Oral, Rat) (A548)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Bromoacetici 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.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Bromoacetic 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.
</health-effects>
  <symptoms>Contact 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.
</symptoms>
  <treatment>EYES: 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.</treatment>
  <created-at type="dateTime">2009-06-22T16:08:35Z</created-at>
  <updated-at type="dateTime">2026-03-31T18:45:35Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>Bromoacetic acid</stitch-id>
  <drugbank-id>DB02198</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OC(=O)CBr</moldb-smiles>
  <moldb-formula>C2H3BrO2</moldb-formula>
  <moldb-inchi>InChI=1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)</moldb-inchi>
  <moldb-inchikey>KDPAWGWELVVRCH-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">138.948</moldb-average-mass>
  <moldb-mono-mass type="decimal">137.931641987</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id>CHEMBL60851</chembl-id>
  <chemspider-id>10301338</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM001527</chemdb-id>
  <dsstox-id>DTXSID7021495</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00010208</susdat-id>
  <iupac>2-bromoacetic acid</iupac>
</compound>
