Lithium bis(trimethylsilyl)amide solution

Name: Lithium bis(trimethylsilyl)amide solution
Brand: ALDRICH

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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Properties

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

Description

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.