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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-H302-H304-H314-H335-H336-H351
Highly flammable liquid and vapour. Harmful if swallowed. May be fatal if swallowed and enters airways. Causes severe skin burns and eye damage. May cause respiratory irritation. May cause drowsiness or dizziness. Suspected of causing cancer.
Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P281-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. 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 ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. 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: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant