Phenyl chloroformate is used in the synthesis of poly(2-(phenoxycarbonyloxy)ethyl methacrylate) and phenyl-(4-vinylphenyl) carbonate. It acts as a precursor of phenyl mixed anhydrides which are used in peptide coupling reactions. It serves as a dehydrating reagent for the conversion of primary amides to nitriles and an intermediate in the synthesis of pharmaceuticals and carbamates.
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Applications
Phenyl chloroformate is used in the synthesis of poly(2-(phenoxycarbonyloxy)ethyl methacrylate) and phenyl-(4-vinylphenyl) carbonate. It acts as a precursor of phenyl mixed anhydrides which are used in peptide coupling reactions. It serves as a dehydrating reagent for the conversion of primary amides to nitriles and an intermediate in the synthesis of pharmaceuticals and carbamates.
Solubility
Miscible with N,N-dimethylformamide.
Notes
Store in cool place. Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with bases, alcohols and amines. Hydrolyses in water.
RUO – Research Use Only
Precursor of phenyl mixed anhydrides, which can be used, e.g. in peptide coupling reactions.
Also used in the cleavage of tertiary amines: J. Chem. Soc. (C), 2015 (1967); cf Ethyl chloroformate, L06311, and 1-Chloroethyl chloroformate, L14197. Review: Synthesis, 1 (1989).
Reagent for dehydration of primary amides to nitriles under mild conditions: Indian J. Chem., 40B, 722 (2001).
Wieting, J. M.; Fisher, T. J.; Schafer, A. G.; Visco, M. D.; Gallucci, J. C.; Mattson, A. E. Preparation and Catalytic Activity of BINOL-Derived Silanediols. Eur. J. Org. Chem. 2015, 2015 (3), 525-533.
Kevill, D. N.; Ryu, Z. H. Correlation of the rates of solvolysis of 2, 1-benzoxathiol-3-one-1, 1-dioxide (2-sulfobenzoic acid cyclic anhydride). J. Chem. Res. 2015, 39 (10), 561-566.