Chemistry:Benzofuran

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Short description: Heterocyclic compound consisting of fused benzene and furan rings
Benzofuran
Skeletal formula with numbering convention
Ball-and-stick model
Space-filling model
Names
Preferred IUPAC name
1-Benzofuran[1]
Other names
Benzofuran[1]
Coumarone
Benzo[b]furan
Identifiers
3D model (JSmol)
107704
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 205-982-6
260881
KEGG
RTECS number
  • DF6423800
UNII
UN number 1993
Properties
C8H6O
Molar mass 118.135 g·mol−1
Melting point −18 °C (0 °F; 255 K)
Boiling point 173 °C (343 °F; 446 K)
Hazards
GHS pictograms GHS02: FlammableGHS08: Health hazard
GHS Signal word Warning
H226, H351, H412
P201, P202, P210, P233, P240, P241, P242, P243, P273, P280, P281, P303+361+353, P308+313, P370+378, P403+235, P405, P501
Lethal dose or concentration (LD, LC):
500 mg/kg (mice).[2]
Related compounds
Related compounds
Benzothiophene, Indole, Indene, 2-Cumaranone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

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

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

Laboratory methods

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

Benzofuran.png

Perkin rearrangement
Diels–Alder reaction yielding a substituted benzofuran|450px
Benzofurans via Cycloisomerization|400px

Related compounds

References

  1. 1.0 1.1 "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 218. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. 
  2. 2.0 2.1 Collin, G.; Höke, H. (2007). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.l03_l01. ISBN 978-3527306732. 
  3. Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone". Organic Syntheses 46: 28. http://www.orgsyn.org/Content/pdfs/procedures/cv5p0251.pdf. ; Collective Volume, 5, pp. 251 
  4. Perkin, W. H. (1870). "XXIX. On some New Bromine Derivatives of Coumarin". Journal of the Chemical Society 23: 368–371. doi:10.1039/JS8702300368. https://zenodo.org/record/2126035. 
  5. Perkin, W. H. (1871). "IV. On some New Derivatives of Coumarin". Journal of the Chemical Society 24: 37–55. doi:10.1039/JS8712400037. https://zenodo.org/record/1848365. 
  6. 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. 
  7. 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. 
  8. Fürstner, Alois; Davies, Paul (2005). "Heterocycles by PtCl2-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes". Journal of the American Chemical Society 127 (43): 15024–15025. doi:10.1021/ja055659p. PMID 16248631.