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Sodium bis(trimethylsilyl)amide is used as a base in organic synthesis as well as to deprotonate other compounds containing weakly acidic O-H, S-H, and N-H bonds. It is used to prepare amines by reacting with alkyl halides. It finds application in certain organic reactions viz. generation of carbenes by dehydrohalogenation of halocarbons and Wittig reagents by deprotonation of phosphonium salts. It accelerates the polymerization of pheneylacetylene in conjunction with rhodium(I) catalysis. Furthermore, it is used for the preparation of lanthanide complexes.
Lis, A. V.; Tsyrendorzhieva, I. P.; Albanov, A. I.; Rakhlin, V. I.; Voronkov, M. G. Migration of trimethylsilyl group in the reaction of sodium bis (trimethylsilyl) amide with bromobenzene. Russ. J. Org. Chem. 2013, 49 (10), 1451-1453.
Zhang, T.; Barclay, L.; Walensky, L. D.; Saghatelian, A. Regulation of mitochondrial ceramide distribution by members of the BCL-2 family. J. Lipid Res. 2015, 56 (8), 1501-1510.
Gefahrenhinweise (EU): H261-H314-H318
In contact with water releases flammable gas. Causes severe skin burns and eye damage. Causes serious eye damage.
Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER/doctor In case of fire: Use for extinction: CO2, sand, extinguishing powder. Store in a dry place.