Benzofuran

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

Benzofuran

Names
IUPAC name 1-Benzofuran
Other names Coumarone, benzo[b]furan
Identifiers
CAS Number	271-89-6 Y
ChEBI	CHEBI:35260 Y
ChEMBL	ChEMBL363614 Y
ChemSpider	8868 Y
DrugBank	DB04179 Y
Jmol 3D model	Interactive image
KEGG	C14512 Y
PubChem	9223
UNII	LK6946W774 Y
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
SMILES o2c1ccccc1cc2
Properties
Chemical formula	C8H6O
Molar mass	118.14 g·mol−1
Melting point	−18 °C (0 °F; 255 K)
Boiling point	173 °C (343 °F; 446 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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.

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 of the resulting ether.

• Perkin rearrangement, where a coumarin is reacted with a hydroxide:

• Diels–Alder reaction of nitro vinyl furans with various dienophiles:

• Cycloisomerization of alkyne ortho-subtituted phenols:

Related compounds

• 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