Benzofuran

Benzofuran
IUPAC name

1-Benzofuran
Other names

Coumarone, benzo[b]furan
Identifiers
CAS number 271-89-6 Y
PubChem 9223
ChemSpider 8868 Y
UNII LK6946W774 Y
DrugBank DB04179
KEGG C14512 Y
ChEBI CHEBI:35260 Y
ChEMBL CHEMBL363614 Y
Jmol-3D images Image 1
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]
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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 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.

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 a hydroxide:

Related compounds

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