Benzofuran

Heterocyclic compound consisting of fused benzene and furan rings From Wikipedia, the free encyclopedia

Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

Quick facts Names, Identifiers ...
Benzofuran
Skeletal formula with numbering convention
Ball-and-stick model
Space-filling model
Names
Preferred IUPAC name
1-Benzofuran[1]
Other names
Benzofuran[1]
Coumarone
Benzo[b]furan
Identifiers
3D model (JSmol)
107704
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.439 Edit this at Wikidata
EC Number
  • 205-982-6
260881
KEGG
RTECS number
  • DF6423800
UNII
UN number 1993
  • InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H checkY
    Key: IANQTJSKSUMEQM-UHFFFAOYSA-N checkY
  • InChI=1/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
    Key: IANQTJSKSUMEQM-UHFFFAOYAU
  • o2c1ccccc1cc2
Properties
C8H6O
Molar mass 118.135 g·mol−1
Melting point −18 °C (0 °F; 255 K)
Boiling point 173 °C (343 °F; 446 K)
Hazards
GHS labelling:
GHS02: FlammableGHS08: Health hazard
Warning
H226, H351, H412
P201, P202, P210, P233, P240, P241, P242, P243, P273, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501
Lethal dose or concentration (LD, LC):
500 mg/kg (mice).[2]
Related compounds
Related compounds
Benzothiophene, Indole, Indene, 2-Cumaranone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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There are benzofuran based herbicides: ethofumesate and benfuresate.[3] Several psychoactive drugs such as 5-MAPB and 6-APB are also derived from benzofuran.

Production

Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.[2]

Laboratory methods

Benzofurans can be prepared by various methods in the laboratory. Notable examples include:

Perkin rearrangement
Diels–Alder reaction yielding a substituted benzofuran
Benzofurans via Cycloisomerization

References

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