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tert-Butyl chloroacetate is used in the synthesis of imidazol-1-yl-acetic acid hydrochloride, cis-disubstituted aziridine ester via aza-Darzens reaction and 1,10-diaza-18-crown-6 based sensors bearing a coumarin fluorophore.
Santosh Kumar Singh.; Narendra Manne.; Purna Chandra Ray.; Manojit Pal. Synthesis of imidazol-1-yl-acetic acid hydrochloride: a key intermediate for zoledronic acid. Beilstein Journal of Organic Chemistry. 2008, 4 42.
E Vedejs.; D W Piotrowski.; F C Tucci. Oxazolium-derived azomethine ylides. External oxazole activation and internal dipole trapping in the synthesis of an aziridinomitosene. Journal of Organic Chemistry. 2000, 65 (18), 5498-5505.
Darzens condensation (see Ethyl chloroacetate, A15554) with carbonyl compounds gives t-butyl glycidic esters, which readily undergo decarboxylative elimination to the homologous aldehydes. See, for example: Rec. Trav. Chim., 89, 18 (1970).
The reaction with imines has also been used in the preparation of aziridines by a nitrogen analogue of the Darzens reaction: J. Chem. Soc., Chem. Commun., 602 (1977).
Hazard Statements: H226-H302-H312-H331-H315-H319-H335
Flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P273-P280h-P305+P351+P338-P309-P310a-P501a
Avoid release to the environment. Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Dispose of contents/container in accordance with local/regional/national/international regulations.