Benzofuran

Benzofuran

Names
Preferred IUPAC name 1-Benzofuran[1]
Other names Benzofuran[1] Coumarone Benzo[b]furan
Identifiers
CAS Number	271-89-6 Y
3D model ( JSmol )	Interactive image
Beilstein Reference	107704
ChEBI	CHEBI:35260 Y
ChEMBL	ChEMBL363614 Y
ChemSpider	8868 Y
DrugBank	DB04179 Y
ECHA InfoCard	100.005.439
EC Number	205-982-6
Gmelin Reference	260881
KEGG	C14512 Y
PubChem CID	9223
RTECS number	DF6423800
UNII	LK6946W774 Y
UN number	1993
CompTox Dashboard (EPA)	DTXSID6020141
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	118.135 g·mol−1
Melting point	−18 °C (0 °F; 255 K)
Boiling point	173 °C (343 °F; 446 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H351, H412
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P273, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501
Lethal dose or concentration (LD, LC):
LD50 (median dose)	500 mg/kg (mice).[2]
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). 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 structural nucleus (parent compound) 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]

• dienophiles:^[7]

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

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