Benzofuran

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This article is about the heterocyclic chemical compound. For its purportedly recreational derivative drug, nicknamed "Benzo Fury", see 6-APB.
Benzofuran
Skeletal formula with numbering convention
Ball-and-stick model Space-filling model
Identifiers
CAS number 271-89-6 YesY
PubChem 9223
ChemSpider 8868 YesY
UNII LK6946W774 YesY
DrugBank DB04179
KEGG C14512 YesY
ChEBI CHEBI:35260 YesY
ChEMBL CHEMBL363614 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H6O
Molar mass 118.13 g mol−1
Melting point −18 °C (0 °F; 255 K)
Boiling point 173 °C (343 °F; 446 K)
Hazards
LD50 500 mg/kg (mice).[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.

Production[edit]

Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.[1]

Laboratory methods[edit]

Benzofurans can be prepared by various methods in the laboratory. Notable examples include:

Perkin rearrangement
Diels–Alder reaction yielding a substituted benzofuran
Benzofurans via Cycloisomerization

Related compounds[edit]

References[edit]

  1. ^ a b Collin, G.; Höke, H. (2007). "Benzofurans". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.l03_l01. 
  2. ^ Burgstahler, A. W.; Worden, L. R. (1966), "Coumarone", Org. Synth. 46: 28 ; Coll. Vol. 5: 251 
  3. ^ Perkin, W. H. (1870). "XXIX. On some New Bromine Derivatives of Coumarin". Journal of the Chemical Society 23: 368–371. doi:10.1039/JS8702300368. 
  4. ^ Perkin, W. H. (1871). "IV. On some New Derivatives of Coumarin". Journal of the Chemical Society 24: 37–55. doi:10.1039/JS8712400037. 
  5. ^ 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. 
  6. ^ Kusurkar, R. S.; Bhosale, D. K. (1990). "Novel Synthesis of Benzosubstituted Benzofurans Via Diels-Alder Reaction". Synthetic Communications 20 (1): 101–109. doi:10.1080/00397919008054620. Retrieved 11 February 2014. 
  7. ^ Fürstner, Alois and Davies, Paul (2005). "Heterocycles by PtCl2-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes". Journal of American Chemical Society 127 (43): 15024–15025. doi:10.1021/ja055659p. Retrieved 11 February 2014.