1-Chloroethyl chloroformate acts as a reagent in the selective N-dealkylation of tertiary amines. It is also used as a reactant in the preparation of alkyl 1-chloroethyl carbonates. Further, it is used for N-demethylation reaction in the determination of multiple drugs of abuse in biological fluids using capillary electrophoresis with native fluorescence and laser-induced fluorescence detection. It plays an important role as a catalyst for the chemoselective desilylation of silyl-protected alcohols. In addition to this, it is used to cleave benzhydryl groups from amines.
Reagent, introduced by Olofson, and found to be superior to other chloroformates for dealkylation of tert-amines, e.g. N-alkylpiperidines to piperidines: J. Org. Chem., 49, 2081, 2795, 2081 (1984). For selective debenzylation of tert-amines, see: Synlett, 195 (1993). For reviews, see: Pure Appl. Chem., 60, 1715 (1988); Synthesis, 1 (1989).
Amata, E.; Bland, N. D.; Campbell, R. K.; Pollastri, M. P. Evaluation of pyrrolidine and pyrazolone derivatives as inhibitors of trypanosomal phosphodiesterase B1 (TbrPDEB1). Tetrahedron Lett. 2015, 56 (21), 2832-2835.
Wang, Z.; Islam, M. J.; Vukotic, V. N. Structural analysis of bis-bispidine tetraazamacrocycle: Long-range weak interactions in a channeled organic crystal. J. Mol. Struct. 2015, 1081, 44-50.
Hazard Statements: H226-H302-H330-H314-H318
Flammable liquid and vapour. Harmful if swallowed. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P201-P280a-P304+P340-P405-P501a
Obtain special instructions before use. Wear protective gloves and eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.