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Ethyl acetoacetate is used as an intermediate in organic synthesis and as a co-promoter for unsaturated polyester resins. It is widely used in the production of dyes, inks, perfumes, plastics and flavoring agents. It is an important starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine and coumarin derivatives. It acts as an intermediate in the synthesis of vitamins and pharmaceuticals. It finds application as a formaldehyde scavenger.
Under the conditions of the classical acetoacetic ester route to methyl ketones [see, e.g.: Org. Synth. Coll., 1, 248, 351 (1941)], varying amounts of O-alkylation occur. Regioselective C-alkylation can be obtained by phase-transfer procedures: J. Org. Chem., 39, 3271 (1974). For improved alkylation using TBAB, see: Org. Prep. Proced. Int., 26, 469 (1994).
Many techniques have been devised for the decarboalkoxylation of substituted ß-ketoesters (compare Diethyl malonate, A15468); for reviews, see: Synthesis, 805, 893 (1982). Enolisable ß-keto esters can be decarboalkoxylated by heating in toluene in the presence of a catalytic amount of DMAP. Other bases are ineffective: J. Org. Chem., 54, 3474 (1989).
For use in diazo transfer reactions, see 4-Acetamidobenzenesulfonyl azide, L15916.
Xu, L.; Jiang, Y. G.; Feng, J. Z.; Feng, J. Influence of Ethyl Acetoacetate on the Structure and Thermal Stability of Alumina Aerogel. Mater. Sci. Forum 2015, 816, 157-162.
Dehghan, A.; Singh, S.; Abbasinejad, M. A.; Hassanabadi, A. Four-component reaction between cyanoacetamide, aryl aldehydes, and ethyl acetoacetate with ammonium carbonate. Res. Chem. Intermed. 2015, 41 (2), 1001-1009.
Hazard Statements: H227-H303-H319
Combustible liquid. May be harmful if swallowed. Causes serious eye irritation.
Precautionary Statements: P210u-P280a-P305+P351+P338-P312a-P403+P235-P501a
Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.