Isopropenyl acetate

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]

Isopropenyl acetate
Names
Other names
1-Methylvinyl acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.239
EC Number
  • 203-562-7
UNII
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).
Infobox references

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
  1. Walters, Michael A.; Lee, Melissa D. (2001). "Isopropenyl Acetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ri077.
  2. 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.
  3. Siegel, Hardo; Eggersdorfer, Manfred (2002). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.
  4. 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.
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