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| 2-Furanone | |
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| IUPAC name | 5H-furan-2-one |
| Identifiers | |
| CAS number | 497-23-4 |
| PubChem | |
| MeSH | |
| SMILES |
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| Properties | |
| Molecular formula | C4H4O2 |
| Molar mass | 84.07336 |
| Density | 1.185 g/cm3, liquid |
| Melting point |
4-5°C1 |
| Boiling point |
86-87°C (@ 12 mm Hg)1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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2-Furanone, also furan-2-one, is a heterocyclic chemical compound classified as a lactone. It is a common component of natural products synthesized by biochemical pathways in organisms, especially plants of the genus Angelica. 2-Furanone is also known as γ-crotonolactone or β-angelica lactone. It is the simplest butenolide compound and is colloquially called "butenolide" in the context of natural product synthesis.
Tautomerism
The tautomer of 2-furanone is known as 2-hydroxyfuran. It is unstable and rarely detected in solution, but 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.
Reactions
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.
References
- ^ a b Sigma-Aldrich Chemicals Product detail
Wikipedia content modification information:
- This page was last modified on 26 August 2008, at 03:11.
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