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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Miscible with dichloromethane, ether, terahydrofuran and protic solvents.
Notes
Moisture sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acids and strong oxidizing agents.
RUO – Research Use Only
General References:
- 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.