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766917

Sigma-Aldrich

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
Beilstein:
3567910
MDL number:
MFCD00008261
UNSPSC Code:
12352111
PubChem Substance ID:
329767270
NACRES:
NA.22

form

liquid

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

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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.

Signal Word

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

Supplementary Hazards

EUH014,EUH019

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Flash Point(F)

31.3 °F - closed cup

Flash Point(C)

-0.4 °C - closed cup

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Nan Li et al.
Lab on a chip, 8(12), 2105-2112 (2008-11-22)
High-density live cell array serves as a valuable tool for the development of high-throughput immunophenotyping systems and cell-based biosensors. In this paper, we have, for the first time, demonstrated a simple fabrication process to form the hexamethyldisilazane (HMDS) and poly(ethylene
Elsa Vennat et al.
Dental materials : official publication of the Academy of Dental Materials, 25(6), 729-735 (2009-01-29)
The objectives of this study were to assess demineralized dentin porosity and quantify the different porous features distribution within the material using mercury intrusion porosimetry (MIP) technique. We compared hexamethyldisilazane (HMDS) drying and lyophilization (LYO) (freeze-drying) in sample preparation. Fifty-six
Nur Hazlin Hazrin-Chong et al.
Journal of microbiological methods, 90(2), 96-99 (2012-05-09)
The use of hexamethyldisilazane (HMDS) as a drying agent was investigated in the specimen preparation for scanning electron microscopy (SEM) imaging of bacterial surface colonization on sub-bituminous coal. The ability of microbes to biofragment, ferment and generate methane from coal
Mario Janjetovic et al.
Chemical communications (Cambridge, England), 49(18), 1826-1828 (2013-01-30)
Sm(HMDS)(2) in n-hexane mediates fast cleavage of primary, secondary and tertiary alkyl fluorides in good to excellent yields. In n-hexane Sm(HMDS)(2) exhibits uniquely enhanced reductive ability towards the C-F bond compared to when using THF as solvent.
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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