Skeletal formula of 2-furanone
Ball-and-stick model of the 2-furanone molecule
IUPAC name
Other names
furan-2-one, γ-crotonolactone, butenolide
497-23-4 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:38118 YesY
ChEMBL ChEMBL166223 YesY
ChemSpider 9917 YesY
ECHA InfoCard 100.007.128
KEGG C17601 YesY
MeSH butenolide
PubChem 10341
Molar mass 84.07336
Density 1.185 g/cm3, liquid
Melting point 4 to 5 °C (39 to 41 °F; 277 to 278 K)[1]
Boiling point 86 to 87 °C (187 to 189 °F; 359 to 360 K) 12 mm Hg[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

2-Furanone, also known as γ-crotonolactone (GCL), is a heterocyclic organic compound. Classified as a lactone, this colourless liquid is colloquially called "butenolide." As a class of compounds, substituted derivatives, which are not in fact prepared from the parent 2-furanone, are called butenolides.

Synthesis and reactions

2-Furanone is prepared by oxidation of furfural:[2]

It exists in equilibrium with the tautomer 2-hydroxyfuran, which serves as an intermediate in the interconversion between the β- and α-furanones. The β form is the more stable. The interconversion is catalyzed by base.

2-Furanones can be converted to furans by a two-step process of reduction followed by dehydration. First the carbon-oxygen double bond is reduced by trimethylsilylation of the oxygen centre.

See also


  1. 1 2 Sigma-Aldrich Chemicals Product detail
  2. Näsman, Jan H. (1990). "3-Methyl-2(5H)-furanone". Organic Syntheses. 68: 162. doi:10.15227/orgsyn.068.0162.

This article is issued from Wikipedia - version of the 10/7/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.