1-(Trimethylsilyl)imidazole acts as a silylating agent for alcohols, carbohydrates and 1,3-dicarbonyl compounds. It is a derivatization reagent used for selective silylation of hydroxyl groups and carboxylic acid without affecting the amino group. It employed as an intermediate for the synthesis of imidazole derivatives. It plays an essential role to synthesize polysubstituted chiral spirotetrahydropyrans. It is also used in the quantification of pintol after derivatization by gas chromatography/ mass spectrometry.
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Applications
1-(Trimethylsilyl)imidazole acts as a silylating agent for alcohols, carbohydrates and 1,3-dicarbonyl compounds. It is a derivatization reagent used for selective silylation of hydroxyl groups and carboxylic acid without affecting the amino group. It employed as an intermediate for the synthesis of imidazole derivatives. It plays an essential role to synthesize polysubstituted chiral spirotetrahydropyrans. It is also used in the quantification of pintol after derivatization by gas chromatography/ mass spectrometry.
Solubility
Miscible with most common organic solvents. It decomposes in water.
Notes
Moisture and light sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents and strong acids.
RUO – Research Use Only
General References:
- Powerful silylating agent (see Appendix 4) for a wide range of functional groups. O-Silylation in the presence of TBAF (0.02 equiv.) occurs under very mild conditions: Tetrahedron Lett., 35, 8409 (1994).
- Acanski, M. M.; Vujic, D. N. Comparing sugar components of cereal and pseudocereal flour by GC-MS analysis. Food Chem. 2014, 145, 743-748.
- Bu, J.; Rhee, H.-K. Silylation of Ti-MCM-41 by trimethylsilyl-imidazole and its effect on the olefin epoxidation with aqueous H2O2. Catal. Lett. 2000, 66 (4), 245-249.
- Jacolot, M.; Jean, M.; Levoin, N.; Weghe, P. The Prins Reaction Using Ketones: Rationalization and Application toward the Synthesis of the Portentol Skeleton. Org. Lett. 2012, 14 (1), 58-61.