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Trichloromethyl chloroformate is used as a reagent in the synthesis of organic compounds. It serves as a source of phosgene used in some laboratory preparations. Also, it is used as a reactant for the synthesis of cyclic carbamimidates, N-alkenyl and cycloalkyl carbamates and prostate-specific membrane antigen-targeted anticancer prodrugs. In addition, it is involved in the preparation of an erythromycin A derivatives and antibody-drug conjugates. It is utilized in the conversion of amines, carboxylic acids, formamides in to isocyanates, acid chlorides and isocyanides respectively.
Convenient replacement for phosgene in many reactions, for example:
Conversion of amines to isocyanates: J. Org. Chem., 41, 2070 (1976); Org. Synth. Coll ., 6, 715 (1988). For aliphatic amines, best results were obtained in the presence of the hindered amine 1,8-Bis(dimethylamino)naphthalene, L00313: J. Org. Chem., 61, 3883 (1996).
Dehydration of N-monosubstituted formamides to isocyanides: Angew. Chem. Int. Ed., 16, 259 (1977).
Formation of nitriles from oximes Synthesis, 1037 (1986); or carboxamides: Tetrahedron Lett., 27, 2203 (1986).
Lezama, J.; Domínguez, R. M.; Chuchani, G. Kinetics of the Gas-Phase Elimination Reaction of Benzyl Chloroformate and Neopentyl Chloroformate. Int. J. Chem. Kinet. 2015, 47 (2), 104-112.
Prousis, K. C.; Markopoulos, J.; Mckee, V.; Igglessi-Markopoulou, O. An efficient synthetic approach towards fully functionalized tetronic acids: the use of 1, 3-dioxolane-2, 4-diones as novel protected-activated synthons of α-hydroxy acids. Tetrahedron 2015, 71 (45), 8637-8648.
Hazard Statements: H330-H314-H318
Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P280-P303+P361+P353-P305+P351+P338-P304+P340-P310a
Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing.