Isopropenyl acetate
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| Other names
1-Methylvinyl acetate
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.003.239 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C5H8O2 | |
| Molar mass | 100.117 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.9090 g/cm3 (20 ºC) |
| Melting point | −92.9 °C (−135.2 °F; 180.2 K) |
| Boiling point | 97 °C (207 °F; 370 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isopropenyl acetate is an organic compound, which is the acetate ester of the enol tautomer of acetone. This colorless liquid is significant commercially as the principal precursor to acetylacetone. In organic synthesis, it is used to prepare enol acetates of ketones and acetonides from diols.[1]
Preparation and reactions
Isopropenyl acetate is prepared by treating acetone with ketene.[2] Upon heating over a metal surface, isopropenyl acetate rearranges to acetylacetone.[3]
- CH2(CH3)COC(O)Me → MeC(O)CH2C(O)Me
Isopropenyl acetate is used to prepare other isopropenyl esters by transesterification.[4]
References
- ^ Walters, Michael A.; Lee, Melissa D. (2001). "Isopropenyl Acetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ri077.
- ^ Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_063. ISBN 978-3527306732.
- ^ Siegel, Hardo; Eggersdorfer, Manfred (2002). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.
- ^ Obora, Yasushi; Ishii, Yasutaka (2012). "Discussion Addendum for: Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate". Org. Synth. 89: 307–310. doi:10.15227/orgsyn.089.0307.