Benzofuran
Appearance
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Names | |||
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IUPAC name
1-Benzofuran
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Other names
Coumarone, benzo[b]furan
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Identifiers | |||
3D model (JSmol)
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ChEBI | |||
ChEMBL | |||
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DrugBank | |||
ECHA InfoCard | 100.005.439 | ||
KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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 | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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500 mg/kg (mice).[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.
Production
Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.[1]
Laboratory methods
Benzofuran can be prepared by O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration of the resulting ether.[2] In another method called the Perkin rearrangement[3][4][5] a coumarin is reacted with a hydroxide:
Related compounds
- Furan, an analog without the fused benzene ring.
- Indole, an analog with a nitrogen instead of the oxygen atom.
- Isobenzofuran, the isomer with oxygen in the adjacent position.
- Aurone
- Thunberginol F
References
- ^ a b Collin, G.; Höke, H. (2007). "Benzofurans". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.l03_l01.
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: CS1 maint: multiple names: authors list (link) - ^ Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone" (PDF). Organic Syntheses. 46: 28
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: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 5, p. 251. - ^ Perkin, W. H. (1870). "XXIX. On some New Bromine Derivatives of Coumarin". Journal of the Chemical Society. 23: 368–371. doi:10.1039/JS8702300368.
- ^ Perkin, W. H. (1871). "IV. On some New Derivatives of Coumarin". Journal of the Chemical Society. 24: 37–55. doi:10.1039/JS8712400037.
- ^ Bowden, K.; Battah, S. (1998). "Reactions of Carbonyl Compounds in Basic Solutions. Part 32. The Perkin Rearrangement". Journal of the Chemical Society, Perkin Transactions 2. 1998 (7): 1603–1606. doi:10.1039/a801538d.
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: CS1 maint: multiple names: authors list (link)