2-Furanone

2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxyisocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for the butenolide class of compounds. It is a colourless liquid.

2-Furanone
Skeletal formula of 2-furanone
Ball-and-stick model of the 2-furanone molecule
Names
Preferred IUPAC name
Furan-2(5H)-one
Other names
Furan-2-one, γ-crotonolactone, butenolide, 5H-furan-2-one
Identifiers
3D model (JSmol)
383585
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.128
EC Number
  • 207-839-3
773828
KEGG
MeSH butenolide
UNII
  • InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 checkY
    Key: VIHAEDVKXSOUAT-UHFFFAOYSA-N checkY
  • InChI=1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
    Key: VIHAEDVKXSOUAT-UHFFFAOYAD
  • O=C\1OC/C=C/1
Properties
C4H4O2
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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

See also
  • Category:Furanones, various substituted structural analogs
  • Pyrone, which has one more carbon atom in the ring

References
  1. 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.


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