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Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

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
Beilstein:
3567910
MDL number:
MFCD00008261
UNSPSC Code:
12352111
PubChem Substance ID:
24853520
NACRES:
NA.22

form

liquid

Quality Level

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

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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.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
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Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H225,H314,H335,H336,H351

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,EUH019

WGK

WGK 2

Flash Point(F)

1.4 °F

Flash Point(C)

-17 °C

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Justyna WK,et al.
Journal of Fluorine Chemistry, 179, 175-178 (2015)
Macromolecules, 39, 5347-5347 (2006)
A Sebok et al.
Journal of chromatography. A, 1211(1-2), 104-112 (2008-10-14)
This paper presents a derivatization, mass fragmentation study relating to the most common six cholic acids, such as cholic, lithocholic, chenodeoxycholic, ursodeoxycholic, 3-hydroxy,7-ketocholanic and dehydrocholic acids, identified and quantified as pollutants in the aquatic environment at the first time. Derivatizations
Hexamethyldisilazane-mediated controlled polymerization of alpha-amino acid N-carboxyanhydrides.
Hua Lu et al.
Journal of the American Chemical Society, 129(46), 14114-14115 (2007-10-30)
Daniele Fabbri et al.
Environmental science & technology, 42(8), 2957-2963 (2008-05-24)
Using the pyrolysis-gas chromatography-mass spectrometry and off-line pyrolysis/silylation methods for lignites from three Miocene brown coal basins of Poland resulted in the characterization of many organic compounds, including dominant cellulose degradation products such as levoglucosan, 1,6-anhydro-beta-D-glucofuranose, and 1,4:3,6-dianhydroglucopyranose. Levoglucosan is
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