sodium bis(trimethylsilyl)azanide

• ChemBase ID: 302111
• Molecular Formular: C6H18NNaSi2
• Molecular Mass: 183.37459
• Monoisotopic Mass: 183.08754693
• SMILES: C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
• Canonical SMILES: C[Si]([N-][Si](C)(C)C)(C)C.[Na+]
• InChI: InChI=1S/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
• InChIKey: WRIKHQLVHPKCJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium bis(trimethylsilyl)azanide
• IUPAC Traditional name: sodium bis(trimethylsilyl)azanide
• Synonyms: NaHMDS; N-Sodiohexamethyldisilazane; Sodium bis(trimethylsilyl)amide, 1M soln. in THF; Sodium hexamethyldisilazane; Sodium bis(trimethylsilyl)amide; Sodium bis(trimethylsilyl)amide, 2M soln. in THF; 双(三甲基硅基)氨化钠, 1M THF溶液; 双(三甲基硅基)氨化钠; 双(三甲基硅基)氨化钠, 2M soln. in THF

Database IDs

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

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.8950769
• LogD (pH = 7.4): -0.8299159
• Log P: 2.7111
• Molar Refractivity: 39.3948 cm^3
• Polarizability: 18.492445 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in hexane, toluene, ether
• Apperance: Crystalline
• Melting Point: 171-175°C
• Flash Point: -17°C(1°F)
• Density: 0.904; 0.920

Safety Information

• Storage Warning: Air & Moisture Sensitive; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: UN2924; UN3096
• Hazard Class: 3; 8
• Packing Group: II
• Risk Statements: 11-14-19-34; 14/15-34
• Safety Statements: 8-16-26-36/37/39-43-45; 8-16-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Hazard statements: H224-H314-H318; H261-H314-H318
• GHS Precautionary statements: P210-P280-P305+P351+P338-P309-P310-P402; P280-P305+P351+P338-P309-P310-P370+P378C-P402

Product Information

• Purity: 98%
• Concentration: 1M soln. in THF; 2M soln. in THF

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).