Isopropenyl acetate

Isopropenyl acetate
Names
	Preferred IUPAC name Prop-1-en-2-yl acetate
	Other names 1-Methylvinyl acetate
Identifiers
CAS Number	108-22-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	7628;
ECHA InfoCard	100.003.239
EC Number	203-562-7;
PubChem CID	7916;
UNII	4AR9LAS337 ;
CompTox Dashboard (EPA)	DTXSID3031492 ;
	InChI InChI=1S/C5H8O2/c1-4(2)7-5(3)6/h1H2,2-3H3 Key: HETCEOQFVDFGSY-UHFFFAOYSA-N;
	SMILES CC(=C)OC(=O)C;
Properties
Chemical formula	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

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

Isopropenyl acetate is prepared by treating acetone with ketene.^[2] Upon heating over a metal surface, isopropenyl acetate rearranges to acetylacetone.^[3]

Reactions

Isopropenyl acetate is used to prepare other isopropenyl ethers.^[4]

Isopropenyl acetate reacts with ketones to give new enol acetates:^[5]

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

References

^ Walters, Michael A.; Lee, Melissa D. (2001). "Isopropenyl Acetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ri077. ISBN 0471936235.
^ 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. ISBN 9783527306732.
^ 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.
^ 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

[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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