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benzofuran

 
Dictionary: ben·zo·fu·ran   (bĕn'zō-fyʊr'ăn', -fyʊ-răn') pronunciation

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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WordNet: benzofuran
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Note: click on a word meaning below to see its connections and related words.

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
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Benzofuran
Chemical structure of benzofuran
Other names Coumarone, benzo[b]furan
Identifiers
CAS number 271-89-6 Yes check.svgY
SMILES
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

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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:

Perkin rearrangement

Related compounds

Safety

The LD50 in mice is 500 mg/kg.[1]

References

  1. ^ a b Gerd Collin, Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi: 10.1002/14356007.l03_l01
  2. ^ Albert W. Burgstahler and Leonard R. Worden “Coumarone” Organic Syntheses, Collected Volume 5, p.251 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0251.pdf
  3. ^ W. H. Perkin, J. Chem. Soc., 1870, 23, 368; 1871, 24, 37.
  4. ^ 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
WordNet. WordNet 1.7.1 Copyright © 2001 by Princeton University. All rights reserved.  Read more
Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Benzofuran" Read more