2-Acetylfuran

2-Acetylfuran

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Names
IUPAC name 1-(2-furanyl)-ethanone
Other names 2-Acetylfuran; Acetyl furan; 2-furyl methyl ketone,
Identifiers
CAS Number	1192-62-7
ChEBI	CHEBI:59983
ChemSpider	13849
Jmol 3D model	Interactive image
PubChem	14505
InChI InChI=1S/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3 Key: IEMMBWWQXVXBEU-UHFFFAOYSA-N InChI=1/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3 Key: IEMMBWWQXVXBEU-UHFFFAOYAG
SMILES CC(=O)C1=CC=CO1
Properties
Chemical formula	C6H6O2
Molar mass	110.11 g·mol−1
Appearance	Low melting solid
Density	1.0975 at 20 °C
Melting point	30 °C (86 °F; 303 K)
Boiling point	168 to 169 °C (334 to 336 °F; 441 to 442 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Acetylfuran is a low melting solid or high boiling liquid, depending on temperature. The solid melts at 30 °C and has a density of 1.0975 g/ml at 20 °C, while the normal boiling point of the liquid is 168–169 °C. 2-Acetylfuran is a useful intermediate in the synthesis of fine chemicals and pharmaceuticals, and is used in the production of the generic cephalophosphorin antibiotic cefuroxime.

Synthesis

2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl Grignard reagent on 2-furonitrile.

Applications

Pharmaceuticals

A one-pot synthesis of an intermediate to the HIV integrase inhibitor S-1360 was based on the Friedel-Crafts alkylation of 2-acetylfuran with 4-fluorobenzyl chloride using zinc chloride catalyst.

Reaction of 2-acetylfuran with aqueous sodium nitrite gave 2-furanyloxoacetic acid, an intermediate to Cefuroxime, a second-generation cephalosporin antibiotic.