Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

766917

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

1.5 M in THF

Synonym(s):

Hexamethyldisilazane lithium salt

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
Beilstein/REAXYS Number:
3567910
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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.

signalword

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

supp_hazards

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 2

flash_point_f

31.3 °F - closed cup

flash_point_c

-0.4 °C - closed cup


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service