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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.
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.
Hazard Statements: H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. 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 if you feel unwell. If skin irritation occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant