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766917

Lithium bis(trimethylsilyl)amide solution

1.5 M in THF

Synonym(s):

Hexamethyldisilazane lithium salt

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About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
4039-32-1
Molecular Weight:
167.33
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
329767270
MDL number:
MFCD00008261
Beilstein/REAXYS Number:
3567910
Concentration:
1.5 M in THF
Form:
liquid
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form

liquid

Quality Segment

100

concentration

1.5 M in THF

density

0.893 g/mL at 25 °C

SMILES string

[Li]N([Si](C)(C)C)[Si](C)(C)C

InChI

1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1

InChI key

YNESATAKKCNGOF-UHFFFAOYSA-N

General description

Lithium bis(trimethylsilyl)amide is commonly used in organic synthesis as a non-nucleophilic strong Bronsted base. It is soluble in most nonpolar solvents such as aromatic hydrocarbons, hexanes, and THF.

Application

Lithium bis(trimethylsilyl)amide can be used as a reagent:     
  • In the deprotonation and nucleophilic difluoromethylation reactions.
  • 3-methoxy substituted dihydropyrrole derivatives by reacting with aldehydes and lithiated methoxyallene via in situ formations of N-trimethylsilylated imines.  
  • In Darzens condensation and directed aldol condensation reactions.      
  • To synthesize poly(N-octyl-p-benzamide)s by chain-growth polycondensation of 4-octylaminobenzoic acid methyl ester.

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Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Self-heat. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

flash_point_f

31.3 °F - closed cup

flash_point_c

-0.4 °C - closed cup

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