The Full Wiki

Benzofuran: Wikis

Advertisements
  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

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]

Advertisements

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

Advertisements






Got something to say? Make a comment.
Your name
Your email address
Message