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Sigma-Aldrich

Bis(trimetilsilil) amida de lítio

1.5 M in THF

Sinônimo(s):

Hexametildissilazano

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About This Item

Fórmula linear:
[(CH3)3Si]2NLi
Número CAS:
4039-32-1
Peso molecular:
167.33
Beilstein:
3567910
Número MDL:
MFCD00008261
Código UNSPSC:
12352111
ID de substância PubChem:
329767270
NACRES:
NA.22

forma

liquid

Nível de qualidade

100

concentração

1.5 M in THF

densidade

0.893 g/mL at 25 °C

cadeia de caracteres SMILES

[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

chave InChI

YNESATAKKCNGOF-UHFFFAOYSA-N

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Descrição geral

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.

Aplicação

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.

Palavra indicadora

Danger

Classificações de perigo

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

Perigos de suplementos

EUH014 - EUH019

Código de classe de armazenamento

4.2 - Pyrophoric and self-heating hazardous materials

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

31.3 °F - closed cup

Ponto de fulgor (°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
Tatsuya Nitabaru et al.
Journal of the American Chemical Society, 131(38), 13860-13869 (2009-09-10)
Full details of an anti-selective catalytic asymmetric nitroaldol reaction promoted by a heterobimetallic catalyst comprised of Nd(5)O(O(i)Pr)(13), an amide-based ligand, and NaHMDS (sodium hexamethyldisilazide) are described. A systematic synthesis and evaluation of amide-based ligands led to the identification of optimum
Juliana Tsz Yan Lee et al.
Scanning, 34(1), 12-25 (2012-04-26)
Common dehydration methods of cells on biomaterials for scanning electron microscopy (SEM) include air drying, hexamethyldisilazane (HMDS) or tetramethysilane (TMS) treatment and critical point drying (CPD). On the other side, freeze-drying has been widely employed in dehydrating biological samples and
Xiaoguang Li et al.
Chemical communications (Cambridge, England), 47(38), 10761-10763 (2011-08-30)
A silica microsphere suspension and a silica sol are employed in a two-step dipping process for the preparation of a superhydrophobic surface. It's not only a facile way to achieve the lotus effect, but can also create a multi-functional surface
Werner Mormann et al.
Macromolecular bioscience, 9(4), 369-375 (2008-11-26)
Trimethylsilylation of cellulose in different 1,3-dialkylimidazolium ionic liquids (IL) with hexamethyldisilazane (HMDS) as a silylating agent was investigated. Trimethylsilyl (TMSi) cellulose with a degree of substitution (DS) greater than 1 is insoluble in the IL. The maximum DS obtained depends
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