Sodium bis(trimethylsilyl)amide, 2M soln. in THF
化学性质
应用
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.
注释
参考文献
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.
GHS危险和防护声明
危险说明（欧盟）:H225-H302-H314-H335-H336-H341b-H351b-H412
Highly flammable liquid and vapour. Harmful if swallowed. Causes severe skin burns and eye damage. May cause respiratory irritation. May cause drowsiness or dizziness. Suspected of causing genetic defects if inhaled Suspected of causing cancer if inhaled Harmful to aquatic life with long lasting effects.
防范说明:P201-P202-P242-P260-P264b-P270-P271-P281-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378r-P403+P233-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Use only non-sparking tools. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. 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. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/ container to an approved waste disposal plant
其他参考资料
文件
产品 SDS
质量分析报告(COA)
产品说明书
