This article is about the heterocyclic chemical compound. For its purportedly recreational derivative drugs, see Benzofury (disambiguation).
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.
^ ab"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. ISBN978-0-85404-182-4.
^ abCollin, G.; Höke, H. (2007). "Benzofurans". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.l03_l01. ISBN978-3527306732.
^Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone" (PDF). Organic Syntheses. 46: 28; Collected Volumes, vol. 5, p. 251.
^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.
March 17, 2024
benzofuran, this, article, about, heterocyclic, chemical, compound, purportedly, recreational, derivative, drugs, benzofury, disambiguation, heterocyclic, compound, consisting, fused, benzene, furan, rings, this, colourless, liquid, component, coal, structural. This article is about the heterocyclic chemical compound For its purportedly recreational derivative drugs see Benzofury disambiguation 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 Benzofuran NamesPreferred IUPAC name 1 Benzofuran 1 Other names Benzofuran 1 CoumaroneBenzo b furanIdentifiersCAS Number 271 89 6 Y3D model JSmol Interactive imageBeilstein Reference 107704ChEBI CHEBI 35260 YChEMBL ChEMBL363614 YChemSpider 8868 YDrugBank DB04179 YECHA InfoCard 100 005 439EC Number 205 982 6Gmelin Reference 260881KEGG C14512 YPubChem CID 9223RTECS number DF6423800UNII LK6946W774 YUN number 1993CompTox Dashboard EPA DTXSID6020141InChI InChI 1S C8H6O c1 2 4 8 7 3 1 5 6 9 8 h1 6H YKey IANQTJSKSUMEQM UHFFFAOYSA N YInChI 1 C8H6O c1 2 4 8 7 3 1 5 6 9 8 h1 6HKey IANQTJSKSUMEQM UHFFFAOYAUSMILES o2c1ccccc1cc2PropertiesChemical formula C 8H 6OMolar mass 118 135 g mol 1Melting point 18 C 0 F 255 K Boiling point 173 C 343 F 446 K HazardsGHS labelling PictogramsSignal word WarningHazard statements H226 H351 H412Precautionary statements P201 P202 P210 P233 P240 P241 P242 P243 P273 P280 P281 P303 P361 P353 P308 P313 P370 P378 P403 P235 P405 P501Lethal dose or concentration LD LC LD50 median dose 500 mg kg mice 2 Related compoundsRelated compounds Benzothiophene Indole Indene 2 CumaranoneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production 1 1 Laboratory methods 2 Related compounds 3 ReferencesProduction editBenzofuran is extracted from coal tar It is also obtained by dehydrogenation of 2 ethylphenol 2 Laboratory methods edit Benzofurans can be prepared by various methods in the laboratory Notable examples include O alkylation of salicylaldehyde with chloroacetic acid followed by dehydration cyclication of the resulting ether and decarboxylation 3 nbsp Perkin rearrangement where a coumarin is reacted with a hydroxide 4 5 6 nbsp Diels Alder reaction clarification needed of nitro vinyl furans with various dienophiles 7 nbsp Cycloisomerization of alkyne ortho substituted phenols 8 nbsp Related compounds editSubstituted benzofurans Dibenzofuran an analog with a second fused benzene ring Furan an analog without the fused benzene ring Indole an analog with a nitrogen instead of the oxygen atom Benzothiophene an analog with a sulfur instead of the oxygen atom Isobenzofuran the isomer with oxygen in the adjacent position Aurone Thunberginol FReferences edit 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 Hoke 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 Furstner Alois amp 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 Retrieved from https en wikipedia org w index php title Benzofuran amp oldid 1213574662, wikipedia, wiki, book, books, library,
