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Fungicides
5-Hydroxy-2(5H)-furanone
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5-Hydroxy-2(5H)-furanone

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5-Hydroxy-2(5H)-furanone
5-Hydroxy-2(5H)-furanone
Names
Preferred IUPAC name
5-Hydroxyfuran-2(5H)-one
Other names
5-Hydroxy-5H-furan-2-one, 2-Hydroxyfuranone-(5), β-oxo-γ-butyrolactone, 4-Oxobut-2-enoic acid, 2,5-dihydrofuran-2-one, beta-Formylacrylic acid lactol, 2-Oxo-5-hydroxy-2,5-dihydrofuran, 2-Hydroxy-2,5-dihydro-5-furanone, 5-Hydroxy-2,5-dihydrofuran-2-one; γ-Hydroxybutenolide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.112.891
PubChem CID
  • InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-3,5H
    Key: DUAZKLYNTLDKQK-UHFFFAOYSA-N
  • C1=CC(=O)OC1O
Properties
C4H4O3
Molar mass 100.073 g·mol−1
Density 1.503 g/mL
Melting point 55 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Hydroxy-2(5H)-furanone is a furanone derived from oxidation of furfural using singlet oxygen. This oxidation is carried out generally in methanol or ethanol with a sensitizer like methylene blue or Rose bengal. The mechanism of this reaction is depicted as below.

Furfural-oxidation.png


Uses

5-Hydroxy-2(5H)-furanone is a potent pesticide and a four carbon building block for various heterocycles.

Chemical properties

5-Hydroxy-2(5H)-furanone exists in chemical equilibrium with its isomer, cis-β-formylacrylic acid, in ring-chain tautomerism:

Tautomer of 5-Hydroxy-2(5H)-furanone.PNG

Under some conditions the compound will isomerize into succinic anhydride. Upon heating in strongly basic solution (pH > 9) this isomer will hydrate to succinic acid.

See also


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