| 2-Furanone | |
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5H-furan-2-one |
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Other names
furan-2-one, γ-crotonolactone, β-angelica lactone, butenolide |
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| Identifiers | |
| CAS number | 497-23-4 |
| PubChem | 10341 |
| ChemSpider | 9917 |
| KEGG | C17601 |
| MeSH | butenolide |
| ChEBI | CHEBI:38118 |
| ChEMBL | CHEMBL166223 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H4O2 |
| Molar mass | 84.07336 |
| Density | 1.185 g/cm3, liquid |
| Melting point |
4-5 °C, 277-278 K, 39-41 °F (Source[1]) |
| Boiling point |
86-87 °C, 359-360 K, 187-189 °F (12 mm Hg, Source[1]) |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
2-Furanone is a heterocyclic organic compound. Classified as a lactone, this colourless liquid is a common natural products synthesized by biochemical pathways, especially plants of the genus Angelica, hence its name β-angelica lactone. It is the simplest butenolide and is colloquially called "butenolide" in the context of natural product synthesis.
2-Furanone is prepared by oxidation of furfural:[2]
It exists in small part as the tautomer 2-hydroxyfuran, which serves as a reactive intermediate in the interconversion between the β and α lactones. The β form is the more stable but interconversion can be catalyzed by the addition of 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 the attachment of a trimethylsilyl functional group to the oxygen atom. The dehydration reaction introduces two carbon-carbon double bonds in the ring.