<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2270</id>
  <title>T3D2266</title>
  <common-name>2-Bromodibenzofuran</common-name>
  <description>2-Bromodibenzofuran (C12H7BrO) is an exogenous organic compound with an average molecular weight of 247.09 g/mol. It exists as a solid at room temperature. 2-Bromodibenzofuran belongs to the dibenzofurans, a subclass of benzofurans within the organic compounds. This organoheterocyclic compound is found in or released from electrical and electronic equipment, specifically conductors or conductive bodies characterized by the conductive materials.

The compound interacts with two recorded protein targets. It binds to the aryl hydrocarbon receptor (AHR), which increases its ability to activate transcription in the XRE promoter region and alters the expression of several genes. Additionally, it targets the transient receptor potential cation channel subfamily A member 1 (TRPA1).</description>
  <cas>86-76-0</cas>
  <pubchem-id>6856</pubchem-id>
  <chemical-formula>C12H7BrO</chemical-formula>
  <weight>245.968030</weight>
  <appearance>Colorless crystals.</appearance>
  <melting-point>110°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Inhalation (L952) ; dermal (L952) ; oral (L952)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>As a strong lachrymator, 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. Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity (not listed by IARC). (L135)</carcinogenicity>
  <use-source>2-Bromodibenzofuran is an industrial chemical. Small amounts may be produced through the production of coal tar or in coal gasification operations. Dibenzofurans are released to the ambient air from combustion sources.  Dibenzofurans may be found in coke dust, grate ash, fly ash, and flame soot.  The general public may be exposed to dibenzofurans through the inhalation of contaminated air or through the consumption of contaminated drinking water or food. Dibenzofurans have been identified in tobacco smoke.
</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>2-Bromodibenzofuran is a lachrymator. 
</health-effects>
  <symptoms>Exposure to eyes can lead to redness and pain.
</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">2009-06-24T20:58:12Z</created-at>
  <updated-at type="dateTime">2026-08-18T21:24:11Z</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>2-Bromodibenzofuran</stitch-id>
  <drugbank-id></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>BrC1=CC=C2OC3=CC=CC=C3C2=C1</moldb-smiles>
  <moldb-formula>C12H7BrO</moldb-formula>
  <moldb-inchi>InChI=1S/C12H7BrO/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-7H</moldb-inchi>
  <moldb-inchikey>CRJISNQTZDMKQD-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">247.087</moldb-average-mass>
  <moldb-mono-mass type="decimal">245.968027493</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id>6595</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>CHEM001967</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00120797</susdat-id>
  <iupac>2-bromodibenzofuran</iupac>
  <moldb-polar-surface-area>13.14</moldb-polar-surface-area>
  <moldb-refractivity>58.84960000000001</moldb-refractivity>
  <moldb-polarizability>21.95455299301549</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>0</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>-3.7125922680132333</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>4.58</moldb-alogps-logp>
  <moldb-alogps-logs>-4.13</moldb-alogps-logs>
  <moldb-alogps-solubility>1.84e-02 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organoheterocyclic compounds</superklass>
  <klass>Benzofurans</klass>
  <subklass>Dibenzofurans</subklass>
  <paper-count type="integer">0</paper-count>
  <sync-id>CED0042974</sync-id>
  <structure-inchikey>CRJISNQTZDMKQD-UHFFFAOYSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:26Z</structure-indexed-at>
</compound>
