Home > Compound List > Product Information
Sodium bis(trimethylsilyl)amide, 2M soln. in THF_Molecular_structure_CAS_1070-89-9)
Click picture or here to close

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

Catalog No. L13352 Name Alfa Aesar
CAS Number 1070-89-9 Website
M. F. C6H18NNaSi2 Telephone
M. W. 183.37459 Fax
Purity Email
Storage Chembase ID: 302111

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 Pictograms GHS02
GHS Pictograms GHS05
GHS Hazard statements H224-H314-H318
European Hazard Symbols Corrosive Corrosive (C)
European Hazard Symbols Flammable 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
Concentration 2M soln. in THF
Density 0.920
Flash Point -17°C(1°F)

DETAILS

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).