Basic information
- Standard SMILES
Brc1ccc2oc3ccccc3c2c1- InChIKey
CRJISNQTZDMKQD-UHFFFAOYSA-N- Molecular formula
- C12H7BrO
- Average molar mass
- 247.09 g/mol
- Monoisotopic mass
- 245.96802694
Overview
2-Bromodibenzofuran is a halogenated dibenzofuran. It is relatively nontoxic although it is irritating to mucous membranes and the upper respiratory tract. It is primarily a laboratory chemical although it can be generated from the production of coal tar or coal gas.
Names & identifiers
- Preferred name
- 2-Bromodibenzofuran
- IUPAC
- 2-bromodibenzofuran
- English name
- 2-Bromodibenzofuran
- Molecular formula
- C12H7BrO
- Molecular weight
- 247.09
Names & synonyms
Show more names
Database identifiers
- CAS
86-76-0- PubChem CID
- 6856
- DTXSID
DTXSID20235337- UNII
- C36TC73SME
- EC Number
- 659-733-5
- Nikkaji
- J405.015K
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 13.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 218
Physicochemical properties
- Melting point
- 121 · 121-122℃
- Boiling point
- 344 ℃ · 344℃
- Density
- 1.577 · 1.577
- refractive index
- 1.529 · 1.5290 (estimate)
- Flash point
- 162 ℃ · 162℃
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in hot methanol.
- form
- Solid
- color
- White to Off-White
- InChI
- InChI=1S/C12H7BrO/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-7H
- InChIKey
- CRJISNQTZDMKQD-UHFFFAOYSA-N
- SMILES
- O1C2=CC=CC=C2C2=CC(Br)=CC=C12
- FDA UNII
- 36 TC73SME · C36TC73SME
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H319-H413
- Precautionary statements
- 264 · P264-P280i-P301+P312a-P305+P351+P338-P337+P313-P501a
- Risk Statements
- 22 · 22-36-53
- Safety Statements
- 26 · 26-36-60-61
- HS Code
- 29329990 · 29329990
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
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.
Toxicity Summary
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.
Safety data
- hs_code
- 29329990
- risk_code
- 22-36-53
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 26-36-60-61
- Hazard statements
- H302-H319-H413
- Precautionary statements
- P264-P280i-P301+P312a-P305+P351+P338-P337+P313-P501a
Chemistry & industry
Uses & manufacturing
Uses
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.
Applications
Description2-Bromo-dibenzofuran is the bromo modified form of dibenzofuran, an aromatic compound consisting two benzene rings fused to a central furan ring. It can be used as a reagent in Friedel-Crafts acylation reactions.
Uses2-Bromodibenzofuran is used as a reagent in Friedel-Crafts acylation reactions.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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