benzofuran
Dictionary:
ben·zo·fu·ran (bĕn'zō-fyʊr'ăn', -fyʊ-răn') 
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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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The noun has one meaning:
Meaning #1:
a colorless oily compound extracted from coal tar and used in manufacturing synthetic resins
Synonyms: coumarone, cumarone
| Wikipedia: Benzofuran |
| Benzofuran | |
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| Other names | Coumarone, benzo[b]furan |
| Identifiers | |
| CAS number | 271-89-6  |
| SMILES |
C1(OC=C2)=C2C=CC=C1
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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 |
| (what is this?) (verify) 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 solid 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.
Contents |
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] a coumarin is reacted with an 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
Safety
The LD50 in mice is 500 mg/kg.[1]
References
- ^ 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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 | coumarone |
| indene (organic chemistry) |
| C8H6O |
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 | 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. Read more |
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| WordNet. WordNet 1.7.1 Copyright © 2001 by Princeton University. All rights reserved. Read more |
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| Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Benzofuran". Read more |
