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Isopropenyl acetate

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Isopropenyl acetate
Names
Preferred IUPAC name Prop-1-en-2-yl acetate
Other names 1-Methylvinyl acetate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.239 Edit this at Wikidata
EC Number
  • 203-562-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H8O2/c1-4(2)7-5(3)6/h1H2,2-3H3Key: HETCEOQFVDFGSY-UHFFFAOYSA-N
SMILES
  • CC(=C)OC(=O)C
Properties
Chemical formula C5H8O2
Molar mass 100.117 g·mol
Appearance Colorless liquid
Density 0.9090 g/cm (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 , 100 kPa). Infobox references
Chemical compound

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.

Preparation

Isopropenyl acetate is prepared by treating acetone with ketene. Upon heating over a metal surface, isopropenyl acetate rearranges to acetylacetone.

Synthese von Acetylaceton

Reactions

Isopropenyl acetate is used to prepare other isopropenyl ethers.

Isopropenyl acetate reacts with ketones to give new enol acetates:

CH2=CH(OAc)CH3 + RC(O)CH3 → CH2=CH(OAc)R + (CH3)2C=O

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. ISBN 978-3527306732.
  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.
  5. Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 1421, ISBN 978-0-471-72091-1
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