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Lithium bis(trimethylsilyl)amide solution

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

1.0 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:

24853520

MDL number:

MFCD00008261

Beilstein/REAXYS Number:

3567910

Concentration:

1.0 M in THF

Form:

liquid

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Properties

form

liquid

Quality Segment

200

concentration

1.0 M in THF

density

0.891 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 (LHMDS) is a non-nucleophilic strong base widely used in organic synthesis for deprotonation reactions and base-catalyzed reactions. It is generally soluble in most nonpolar organic solvents.

Application

Lithium bis(trimethylsilyl)amide solution (1.0 M in THF) can be used as a base:

To catalyze polymerization reaction in the synthesis of poly(p-benzamide)s.
In the synthesis of cyclic poly(α-peptoid)s and α-(difluoromethyl)styrene.
In directed aldol condensations and Darzens condensation reactions; α-arylation of aryl ester derivatives and allylic amination reaction.
For the generation of kinetic enolates than sodium hexamethyldisilazide (NaHMDS) because the enolates produced are more regiostable than those produced with NaHMDS.