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Lithium bis(trimethylsilyl)amide is used in generating enolates for preparing lactone precursors, pyranones, and cyclohexanes. It is used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines and in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles. It is also used in the lithiation of ethyl acetate and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones.
Bert Y. Kimura.; Theodore L. Brown. Solvent effects on the aggregation of lithium bis(trimethylsilyl)amide. Journal of Organometallic Chemistry. 1971, 26 (1), 57-67.
Sunwoo Lee.; Morten Jørgensen.; John F. Hartwig. Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides and Lithium Bis(trimethylsilyl)amide as an Ammonia Equivalent. Org. Lett. 2001, 3 (17), 2729-2732.
Supplied in septum cap bottle.
Versatile non-nucleophilic strong base. For examples of use in the lithiation of ethyl acetate, see: Org. Synth. Coll., 6, 598 (1988), and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones: Org. Synth. Coll., 9, 442 (1998).
Hazard Statements: H225-H303-H333-H314-H318-H351-H335-H373
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. May cause damage to organs through prolonged or repeated exposure.
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.