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Ethyl chloroacetate is a reagent used in the preparation of 5 member heterocycles. It is used as pharmaceutical and organic intermediate. It is used as a solvent for organic synthesis.
J Q Liu, T Kurihara; M Miyagi; S Tsunasawa; M Nishihara; N Esaki; K Soda. Paracatalytic inactivation of L-2-haloacid dehalogenase from Pseudomonas sp. YL by hydroxylamine. Evidence for the formation of an ester intermediate. Journal of Biological Chemistry. 1997, 272 (6), 3363-3368.
Andrew J Moad; Lee J Klein; Dennis G Peters; Jonathan A Karty; James P Reilly. Catalytic reduction of ethyl chloroacetate by cobalt(I) salophen electrogenerated at vitreous carbon cathodes. Journal of Electroanalytical Chemistry. 2002, 531, (2), 163-169.
For examples of use in the Darzens reaction with carbonyl compounds to give glycidic esters, see: Org. Synth. Coll., 3, 727 (1955); 4, 459 (1963); reviews: Org. React., 5, 413 (1949); Chem. Rev., 55, 283 (1955). In the presence of base, glycidic esters rearrange to ɑ-substituted aldehydes: Org. Synth. Coll., 3, 733 (1955):
For a theoretical study of a proposed cyclic transition state in the Darzens reaction, see: J. Org. Chem., 61, 6723 (1996).
Undergoes phase-transfer catalyzed carbene-like addition to activated alkenes to give cyclopropane derivatives: Synth. Commun., 22, 1651 (1992):
Compare (±)-2-Chloropropionic acid, A12860, for a similar reaction.
Gefahrenhinweise (EU): H226-H301-H311-H331
Flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.