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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.
Hazard Statements: H226-H300-H311+H331-H315-H317-H318
Flammable liquid and vapour. Fatal if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P270-P271-P272-P280-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P310-P311-P312-P330-P333+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing 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. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant