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Sigma-Aldrich

Lithium-bis-(trimethylsilyl)-amid -Lösung

1.5 M in THF

Synonym(e):

Hexamethyldisilazan Lithiumsalz

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About This Item

Lineare Formel:
[(CH3)3Si]2NLi
CAS-Nummer:
4039-32-1
Molekulargewicht:
167.33
Beilstein:
3567910
MDL-Nummer:
MFCD00008261
UNSPSC-Code:
12352111
PubChem Substanz-ID:
329767270
NACRES:
NA.22

Form

liquid

Konzentration

1.5 M in THF

Dichte

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

InChIKey

YNESATAKKCNGOF-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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.

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Central nervous system, Respiratory system

Zusätzliche Gefahrenhinweise

EUH014,EUH019

Lagerklassenschlüssel

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Flammpunkt (°F)

31.3 °F - closed cup

Flammpunkt (°C)

-0.4 °C - closed cup

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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
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
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.
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)
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