[L13352] CAS 1070-89-9 | Sodium bis(trimethylsilyl)amide, 2M soln. in THF

CAS : 1070-89-9
UN# : UN2924
MDL : MFCD00009835
Hazard Class : 3
EINECS : 213-983-8
Packing Group : II

Other name :

NaHMDSN-Sodiohexamethyldisilazane

Chemical Properties

Formula : C6H18NNaSi2
Formula weight : 183.38
Flash point : -17°(1°F)
Density : 0.920
Sensitivity : Moisture Sensitive. May form a Precipitate. Store under Nitrogen. Ambient temperatures.
Form : Liquid
Solubility : Miscible with benzene and toluene.

Literature References

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).

Notes

Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents, strong oxidizing agents and oxygen. Dry residue is explosive.Other References:Beilstein: 3629917UN#: UN2924

Grade Specifications

Grade Specifications

Hazard Statements : H224-H314-H318Extremely flammable liquid and vapour.Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P210-P280-P305+P351+P338-P309-P310-P402Keep away from heat/sparks/open flames/hot surfaces. – No smoking.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 or doctor/physician.Store in a dry place.