766917
Lithium bis(trimethylsilyl)amide solution
1.5 M in THF
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Synonym(s):
Hexamethyldisilazane lithium salt
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
Recommended Products
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
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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.
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
wgk_germany
WGK 2
flash_point_f
31.3 °F
flash_point_c
-0.4 °C
Certificates of Analysis (COA)
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'Conventional' (-)-sparteine adducts of lithium and sodium 1,1,1,3,3,3-hexamethyldisilazide (HMDS) were prepared and characterised, along with an unexpected and 'unconventional' hydroxyl-incorporated sodium sodiate, [(-)-sparteine x Na(mu-HMDS)Na x (-)-sparteine](+)[Na(4)(mu-HMDS)(4)(OH)](-)--the complex anion of which is the first inverse crown ether anion.
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