Sodium bis(trimethylsilyl)amide, 2M soln. in THF

• Catalog No.: L13352
• CAS Number: 1070-89-9
• M. F.: C6H18NNaSi2
• M. W.: 183.37459

SYNONYMS

• Title: 双(三甲基硅基)氨化钠, 2M soln. in THF
• IUPAC name: sodium bis(trimethylsilyl)azanide
• IUPAC Traditional name: sodium bis(trimethylsilyl)azanide
• Synonyms: N-Sodiohexamethyldisilazane; NaHMDS

DATABASE IDS

• Beilstein Number: 3629917
• EC Number: 213-983-8
• MDL Number: MFCD00009835
• CAS Number: 1070-89-9

PROPERTIES

• Hazard Class: 3
• UN Number: UN2924
• Packing Group: II
• GHS Hazard statements: H224-H314-H318
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P280-P305+P351+P338-P309-P310-P402
• Risk Statements: 11-14-19-34
• Safety Statements: 8-16-26-36/37/39-45
• Storage Warning: Air & Moisture Sensitive
• TSCA Listed: 是
• Concentration: 2M soln. in THF
• Density: 0.920
• Flash Point: -17°C(1°F)

REFERENCES

• 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).
• Useful sterically hindered base (NaHMDS) for, e.g. generation of enolates, Wittig reagents or carbenes.
• 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).