TCI C1396 Chloromethyl Chloroformate (CAS 22128-62-7) is a reactive chloroformate carrying an additional chloromethyl electrophilic site. Reaction with alcohols or amines gives chloromethyl carbonates and carbamates, whose remaining chloromethyl group can then be displaced by carboxylate, amine, or thiol nucleophiles. This two-step strategy is widely used to build acyloxymethyl and carbonate-type prodrug linkers in medicinal chemistry. Available from AMI Scientific in 25 g and 100 g packs, the reagent is corrosive and moisture-sensitive and must be handled under anhydrous conditions in a fume hood.
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- Hagen et al. (1998). Structure and Conformational Composition of Chloromethyl Chloroformate: An Electron-Diffraction and ab Initio Molecular Orbital Investigation. The Journal of Physical Chemistry A doi:10.1021/jp981744q
- Jogender et al. (2020). A DFT-D2 study on the adsorption of phosgene derivatives and chloromethyl chloroformate on pristine and Fe4-decorated graphene. Journal of Molecular Graphics and Modelling doi:10.1016/j.jmgm.2020.107754
- Lu et al. (2019). Release, Separation, and Recovery of Monomeric Reducing N-Glycans with Pronase E Combined with 9-Chloromethyl Chloroformate and Glycosylasparaginase. Biochemistry doi:10.1021/acs.biochem.8b01224
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