Benzofuran

Benzofuran
Ball-and-stick model	Space-filling model
Names
	Preferred IUPAC name 1-Benzofuran[1]
	Other names Benzofuran[1]; Coumarone; Benzo[b]furan
Identifiers
CAS Number	271-89-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35260 ;
ChEMBL	ChEMBL363614 ;
ChemSpider	8868 ;
DrugBank	DB04179 ;
ECHA InfoCard	100.005.439
KEGG	C14512 ;
PubChem CID	9223;
UNII	LK6946W774 ;
CompTox Dashboard (EPA)	DTXSID6020141 ;
	InChI InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H Key: IANQTJSKSUMEQM-UHFFFAOYSA-N ; InChI=1/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H Key: IANQTJSKSUMEQM-UHFFFAOYAU;
	SMILES o2c1ccccc1cc2;
Properties
Chemical formula	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
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	500 mg/kg (mice).[2]
Related compounds
Related compounds	Benzothiophene, Indole, Indene
	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

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:

O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation.[3]

Perkin rearrangement, where a coumarin is reacted with a hydroxide:[4][5][6]

Diels–Alder reaction of nitro vinyl furans with various dienophiles:[7]

Cycloisomerization of alkyne ortho-substituted phenols:[8]

Related compounds

Substituted benzofurans
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 F
Benzofuran Schiff base

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References

"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.
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.; Collective Volume, 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.

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[iupac2013-1] "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.

[Ullmann-2] 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.; Collective Volume, 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.