Heterocyclic compound consisting of fused benzene and furan rings
This article is about the heterocyclic chemical compound. For its purportedly recreational derivative drugs, see
Benzofury (disambiguation) .
Benzofuran Names Preferred IUPAC name Other namesBenzofuran
[ 1] Coumarone
Benzo[
b ]furan
Identifiers 107704 ChEBI ChEMBL ChemSpider DrugBank ECHA InfoCard 100.005.439 EC Number 260881 KEGG RTECS number UNII UN number 1993 InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
Y Key: IANQTJSKSUMEQM-UHFFFAOYSA-N
Y InChI=1/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
Key: IANQTJSKSUMEQM-UHFFFAOYAU
Properties C 8 H 6 O Molar mass −1 Melting point −18 °C (0 °F; 255 K) Boiling point 173 °C (343 °F; 446 K) Hazards GHS labellingWarning 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).
Chemical compound
Benzofuran is theheterocyclic compound consisting of fusedbenzene andfuran rings. This colourless liquid is a component ofcoal 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.
Benzofuran is extracted from coal tar. It is also obtained bydehydrogenation of 2-ethylphenol .[ 2]
Benzofurans can be prepared by various methods in the laboratory. Notable examples include:
^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 ^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 ^ Burgstahler, A. W.; Worden, L. R. (1966)."Coumarone" (PDF) .Organic Syntheses 46 : 28 Collected Volumes , vol. 5, p. 251^ Perkin, W. H. (1870)."XXIX. On some New Bromine Derivatives of Coumarin" .Journal of the Chemical Society 23 :368– 371.doi :10.1039/JS8702300368 .^ Perkin, W. H. (1871)."IV. On some New Derivatives of Coumarin" .Journal of the Chemical Society 24 :37– 55.doi :10.1039/JS8712400037 .^ 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 . ^ 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 . ^ 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 .
1 ring
Three-membered Five-membered Six-membered Seven-membered Nine-membered 18-membered
2 rings
Five + Five Five + Six Six + Six Five + Seven
