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Sodium bis(trimethylsilyl)amide is a strong base used in organic synthesis for deprotonation reactions and base catalyzed reaction. It is also used to enhance the polymerization of pheneylacetylene in conjunction with rhodium(I) catalysis. It is involved in the generation of enolates, Wittig reagents and carbenes.
Useful sterically hindered base (NaHMDS) for, e.g. generation of enolates, Wittig reagents or carbenes.
Used as a base for the preparation of ester enolates: J. Am. Chem. Soc., 93, 4945 (1971). Has been found to be superior to LDA for preparation of (Z)-enolates of ketones under thermodynamic control: Tetrahedron Lett., 30, 2779 (1989).
In the Wittig reaction, gives Li salt-free product distribution patterns, with selective (Z)-alkene formation: Chem. Ber., 109, 1694 (1976); Tetrahedron Lett., 30, 2173 (1989). For formation of anions of benzylic phosphonates and subsequent ɑɑ-difluorination, see N-Fluorobenzenesulfonimide, L13955.
Found to give better yields than LiHMDS or KHMDS for the carbenoid reactions with Dibromomethane, A10456: Synthesis, 201 (1972); Angew. Chem. Int. Ed., 11, 326 (1972).
Sufficiently nucleophilic to act as a protected form of ammonia in the synthesis of primary amines from halides and tosylates: Chem. Ber., 117, 1250 (1984).
Lis, A. V.; Tsyrendorzhieva, I. P.; Albanov, A. I.; Shainyan, B. A.; Rakhlin, V. I. Reaction of sodium bis(trimethylsilyl) amide with bromotoluenes. Russ. J. Org. Chem. 2015, 51 (3), 335-340.
Block, M.; Bette, M.; Wagner, C.; Schmidt, J.; Steinborn, D. Rhodium(I) complexes with κP coordinated ω-phosphinofunctionalized alkyl phenyl sulfide, sulfoxide and sulfone ligands and their reactions with sodium bis (trimethylsilyl) amide and Ag [BF4]. J. Org. Chem. 2011, 696 (9), 1768-1781.
Hazard Statements: H225-H303-H333-H314-H318-H351-H335
Highly flammable liquid and vapour. May be harmful if swallowed. May be harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of causing cancer. May cause respiratory irritation.
Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.