Benzofuran

Benzofuran
Names
	Preferred IUPAC name 1-Benzofuran
	Other names Benzofuran; Coumarone; Benzo[b]furan
Identifiers
CAS Number	271-89-6 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	107704
ChEBI	CHEBI:35260 ;
ChEMBL	ChEMBL363614 ;
ChemSpider	8868 ;
DrugBank	DB04179 ;
EC Number	205-982-6;
Gmelin Reference	260881
KEGG	C14512 ;
PubChem CID	9223;
RTECS number	DF6423800;
UNII	LK6946W774 ;
UN number	1993
	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
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H351, H412
GHS precautionary statements	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):
LD50 (median dose)	500 mg/kg (mice).
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).
	verify (what is ?)
	Infobox references

Short description: Heterocyclic compound consisting of fused benzene and furan rings

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^{[clarification needed]} of nitro vinyl furans with various dienophiles:^[7]

Diels–Alder reaction yielding a substituted benzofuran|450px

Cycloisomerization of alkyne ortho-substituted phenols:^[8]

Benzofurans via Cycloisomerization|400px

Related compounds

Substituted 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 F

References

↑ ^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.
↑ ^2.0 ^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.
↑ 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
↑ 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.
↑ 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.
↑ 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. PMID 16248631.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Benzofuran. Read more

[iupac2013-1] 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.

[Ullmann-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.