2-Bromodibenzofuran

HCID 6856CAS 86-76-0

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

2-Bromodibenzo[b,d]furan2-BROMODIBENZOFURANNSC 1735DTXSID202353372-Bromodibenzo(b,D)furan4-bromo-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaene4-bromo-8-oxatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaeneRefChem:85862Dibenzofuran, 2-bromo-(8CI)DTXCID20157828Dibenzofuran, 2-bromo-(8CI)(9CI)659-733-5
Show more names
4,4,5,5-tetramethyl-2-(3-(6-phenyldibenzo[b,d]thiophen-4-yl)phenyl)-1,3,2-dioxaborolaneDBF-Brc2-DCDF-A2-bromo-dibenzouran2-Bromodibenzofuran >2-MONOBROMODIBENZOFURAN
CRJISNQTZDMKQD-UHFFFAOYSA-N86-76-02-BROMO-DIBENZOFURANDibenzofuran, 2-bromo-MFCD00092338NSC-1735C36TC73SMENSC1735

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

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Hazard Classes and CategoriesAcute Tox. 4 (97.6%)

Toxicology

Treatment · 1 item

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.

Health Effects2-Bromodibenzofuran is a lachrymator.
Exposure RoutesInhalation (L952) ; dermal (L952) ; oral (L952)
Toxicity Summary · 1 item

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.

Signs and SymptomsExposure to eyes can lead to redness and pain.
Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)

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

Chemistry & industry

Uses & manufacturing

Uses · 1 item

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.

Suppliers50 total

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
BAYNOE CHEM CO.,LTD+86-21-34783353 +8615000719740 · [email protected]
郑州圣壹新材料科技有限公司0371-63891666 18037898020 · [email protected]

Related reactions

23 records

Linked notes

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