Benzofuran Identifiers CAS number PubChem ChemSpider UNII DrugBank KEGG ChEBI ChEMBL Jmol-3D images Image 1 Properties Molecular formula C8H6O Molar mass 118.13 g mol−1 Melting point
-18 °C, 255 K, -0 °F
173 °C, 446 K, 343 °F
Hazards LD50 500 mg/kg (mice). (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.
Benzofuran can be prepared by O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration of the resulting ether. In another method called the "Perkin rearrangement" a coumarin is reacted with a hydroxide:
- 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.
- Thunberginol F
- ^ a b Gerd Collin, Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi: 10.1002/14356007.l03_l01
- ^ Albert W. Burgstahler and Leonard R. Worden “Coumarone” Organic Syntheses, Collected Volume 5, p.251 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0251.pdf
- ^ W. H. Perkin, J. Chem. Soc., 1870, 23, 368; 1871, 24, 37.
- ^ Reactions of carbonyl compounds in basic solutions. Part 32.1 The Perkin rearrangement Keith Bowden and Sinan Battah J. Chem. Soc., Perkin Trans. 2, 1998, 1603 - 1606, doi:10.1039/a801538d
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