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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.
Hazard Statements: H301-H311-H314-H335
Toxic if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage. May cause respiratory irritation.
Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant