benzofuran
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ben·zo·fu·ran
(bĕn'zō-fyʊr'ăn', -fyʊ-răn') 
n.
A colorless liquid, C8H6O, found in coal tar and used to make thermoplastic resins for paints and varnishes. Also called coumarone.
n.
A colorless liquid, C8H6O, found in coal tar and used to make thermoplastic resins for paints and varnishes. Also called coumarone.
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Benzofuran
This article is about the heterocyclic chemical compound. For its purportedly recreational derivative drug, nicknamed "Benzo Fury", see 6-APB.
| Benzofuran | |
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1-Benzofuran |
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Other names
Coumarone, benzo[b]furan |
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| Identifiers | |
| CAS number | 271-89-6  |
| PubChem | 9223 |
| ChemSpider | 8868 |
| UNII | LK6946W774 |
| DrugBank | DB04179 |
| KEGG | C14512 |
| ChEBI | CHEBI:35260 |
| ChEMBL | CHEMBL363614 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H6O |
| Molar mass | 118.13 g mol−1 |
| Melting point |
-18 °C, 255 K, -0 °F |
| Boiling point |
173 °C, 446 K, 343 °F |
| Hazards | |
| LD50 | 500 mg/kg (mice).[1] |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.
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Contents
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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.
- ^ Burgstahler, A. W.; Worden, L. R. (1966), "Coumarone", Org. Synth. 46: 28, http://www.orgsyn.org/orgsyn/pdfs/CV5P0251.pdf; Coll. Vol. 5: 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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American Heritage Dictionary
The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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