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Ethyl 4-chloroacetoacetate is used as a precursor in the preparation of phosphorous ylides. It finds application in regular film coating, pharmaceutical coating and formulation.
Reacts at the 2-position with isocyanates in the presence of base to give 2-aminofuranone derivatives via a ketene N-acetal intermediate: Chem. Ber., 109, 212 (1976):
Isothiocyanates similarly give 2-aminothiophenones: J. Chem. Soc., Perkin 1, 1078 (1981).
Acid-catalyzed reaction with phenols gives 3-(chloromethyl)coumarins, readily convertible to benzofuran-3-acetic acids: Heterocycles, 41, 647 (1995):
Roslan, I. I.; Lim, Q. X.; Han, A.; Chuah, G. K.; Jaenicke, S. Solvent-Free Synthesis of 4H-Pyrido[1,2-a]pyrimidin-4-ones Catalyzed by BiCl3: A Green Route to a Privileged Backbone. Eur. J. Org. Chem. 2015, 2015 (11), 2351-2355.
Wang, Y. J.; Liu, X. Q.; Luo, X.; Liu, Z. Q.; Zheng, Y. G. Cloning, expression and enzymatic characterization of an aldo-keto reductase from Candida albicans XP1463. J. Mol. Catal. B: Enzym. 2015, 122, 44-50.
Gefahrenhinweise (EU): H227-H301-H314-H318
Combustible liquid. Toxic if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.