Benzofuran

This article is about the heterocyclic chemical compound. For its purportedly recreational derivative drug, nicknamed "Benzo Fury", see 6-APB.

Benzofuran
IUPAC name 1-Benzofuran
Other names Coumarone, benzo[b]furan
Identifiers
CAS number	271-89-6 Y
PubChem	9223
ChemSpider	8868 Y
UNII	LK6946W774 Y
DrugBank	DB04179
KEGG	C14512 Y
ChEBI	CHEBI:35260 Y
ChEMBL	CHEMBL363614 Y
Jmol-3D images	Image 1
SMILES o2c1ccccc1cc2
InChI 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
Molecular formula	C8H6O
Molar mass	118.13 g mol−1
Melting point	-18 °C, 255 K, -0 °F
Boiling point	173 °C, 446 K, 343 °F
Hazards
LD50	500 mg/kg (mice).[1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.^[1]

Laboratory methods

Benzofuran can be prepared by O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration of the resulting ether.^[2] In another method called the "Perkin rearrangement"^[3][4] a coumarin is reacted with a hydroxide:

Related compounds

• Furan, an analog without the fused benzene ring.
• Indole, an analog with a nitrogen instead of the oxygen atom.
• Isobenzofuran, the isomer with oxygen in the adjacent position.
• Aurone
• Thunberginol F

References

1. ^ ^{a b} Gerd Collin, Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi: 10.1002/14356007.l03_l01
2. ^ Albert W. Burgstahler and Leonard R. Worden “Coumarone” Organic Syntheses, Collected Volume 5, p.251 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0251.pdf
3. ^ W. H. Perkin, J. Chem. Soc., 1870, 23, 368; 1871, 24, 37.
4. ^ Reactions of carbonyl compounds in basic solutions. Part 32.1 The Perkin rearrangement Keith Bowden and Sinan Battah J. Chem. Soc., Perkin Trans. 2, 1998, 1603 - 1606, doi:10.1039/a801538d