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Trichloroacetyl isocyanate is used as an in-situ derivatizing reagent for characterization of alcohols, glycols, phenols, and amines by nuclear magnetic resonance. It is also used in anion chemical ionization mass spectrometry and in catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrate. Further, it serves as a reagent for the conversion of alcohols into carbamates.
Reacts with nucleophiles to give ureas, carbamates, etc., from which the trichloroacetyl group can readily be removed. For reaction of acyl isocyanates with Grignard reagents to give primary carboxamides, see: Tetrahedron Lett., 981 (1975).
[2+2]-Cycloaddition with cyclic enol ethers gives fused azetidinones: Tetrahedron, 45, 227 (1989).
Causes characteristic chemical shifts in the ɑ-protons of alcohols by in situ conversion to the carbamates: Anal. Chem., 431 (1965).
Reviews: Chemistry of ɑ-haloisocyanates: Synthesis, 85 (1980). General isocyanate chemistry: Appendix 3.
Shajari, N.; Kazemizadeh, A. R.; Ramazani, A.; Joo, S. W.; Ślepokura, K.; Lis, T.; Souldozi, A. Facile synthesis and crystal structure of 1,5-dimethyl-6-thioxo-1,3,5-triazinane-2,4-dione. J. Struct. Chem. 2015, 56 (4), 806-810.
Szcześniak, P.; Stecko, S. An approach to asymmetric synthesis of beta-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement. RSC Adv. 2015, 5 (39), 30882-30888.
Dichiarazioni di rischio (UE): H227-H330-H314-H318-H334
Combustible liquid. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. May cause allergy or asthma symptoms or breathing difficulties if inhaled.
Dichiarazioni precauzionali: 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.