766917
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:
Molecular Weight:
167.33
Beilstein:
3567910
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.
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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 Statements
Precautionary Statements
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
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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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
Haoyu Tang et al.
Biomacromolecules, 11(6), 1585-1592 (2010-05-15)
A series of poly(gamma-chloropropyl-L-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5-28 kg x mol(-1)) and molecular weight distribution (PDI = 1.16-1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of gamma-chloropropyl-L-glutamic acid based N-carboxylanhydride (CP-NCA). CD, FTIR
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
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
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
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