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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.
Hazard Statements: H227-H301+H311+H331-H314-H318-H334-H335
Combustible liquid. Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P261-P264b-P270-P271-P280-P285-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P310-P311-P312-P330-P331-P363-P374-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. In case of inadequate ventilation wear respiratory protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Fight fire with normal precautions from a reasonable distance. Dispose of contents/ container to an approved waste disposal plant