TSIM - N-Trimethylsilyl-imidazole
M 140.3 g/mol, Bp 94-96°C (760 mm Hg), density d20°/4° = 0.961
Strongest hydroxyl silylator; reagent of choice for carbohydrates and most steroids (even strongly hindered steroids) It is remarkable that TSIM reacts quickly and smooth with hydroxyl (even tert. OH) and carboxyl groups, but not with amines. Hence it is especially suited for multiple derivatizations, when compounds with various functional groups are to be derivatized in different ways (e.g., -O-TMS, -N-HFB derivatives of catecholamines).
Recommended applications: alcohols, phenols, organic acids, steroids, hormones, glycols, nucleotides, narcotics.