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
Preferred IUPAC name
Prop-1-en-2-yl acetate
Other names
1-Methylvinyl acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.239
EC Number
  • 203-562-7
UNII
  • InChI=1S/C5H8O2/c1-4(2)7-5(3)6/h1H2,2-3H3
    Key: HETCEOQFVDFGSY-UHFFFAOYSA-N
  • CC(=C)OC(=O)C
Properties
C5H8O2
Molar mass 100.117 g·mol−1
Appearance Colorless liquid
Density 0.9090 g/cm3 (20 °C)
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]

Synthese von Acetylaceton

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. ISBN 0471936235.
  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. ISBN 9783527306732.
  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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