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Benzofuran

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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
ECHA InfoCard 100.005.439 Edit this at Wikidata
EC Number
  • 205-982-6
260881
KEGG
RTECS number
  • DF6423800
UNII
UN number 1993
  • InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H checkY
    Key: IANQTJSKSUMEQM-UHFFFAOYSA-N checkY
  • InChI=1/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
    Key: IANQTJSKSUMEQM-UHFFFAOYAU
  • o2c1ccccc1cc2
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 labelling:
GHS02: FlammableGHS08: Health hazard
Warning
H226, H351, H412
P201, P202, P210, P233, P240, P241, P242, P243, P273, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, 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).
checkY verify (what is checkY☒N ?)

Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

Production

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

Laboratory methods

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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
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References

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  1. ^ a b "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. ^ a b Collin, G.; Höke, H. (2007). "Benzofurans". 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" (PDF). Organic Syntheses. 46: 28; Collected Volumes, vol. 5, p. 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.
  5. ^ Perkin, W. H. (1871). "IV. On some New Derivatives of Coumarin". Journal of the Chemical Society. 24: 37–55. doi:10.1039/JS8712400037.
  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. hdl:11858/00-001M-0000-0025-AA5A-1. PMID 16248631.