324620
Lithium bis(trimethylsilyl)amide
97%
Synonym(s):
Hexamethyldisilazane lithium salt
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About This Item
Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
EC Number:
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
solid
density
0.860 g/mL at 25 °C (lit.)
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 a non-nucleophilic strong Brønsted base, which is generally soluble in most of the nonpolar organic solvents. It is most commonly employed in organic reactions.
Application
Base employed in generating enolates for the preparation of lactone precursors, pyranones, and cyclohexanes.
Used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines. Also used in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles.
Used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines. Also used in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B
Supplementary Hazards
Storage Class Code
4.2 - Pyrophoric and self-heating hazardous materials
WGK
WGK 2
Flash Point(F)
62.6 °F - closed cup
Flash Point(C)
17 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Lithium Bis(trimethylsilyl)amide and Tris(trimethylsilyl)amine
Inorganic Syntheses (1966)
The Journal of Organic Chemistry, 58, 7304-7304 (1993)
Wen-Xiong Zhang et al.
Chemical communications (Cambridge, England), (36), 3812-3814 (2006-09-14)
Organo alkali metal compounds such as (n)BuLi and (Me3Si)2NK act as excellent catalyst precursors for the addition of phosphine P-H bonds to carbodiimides, offering a general and atom-economical route to substituted phosphaguanidines, with excellent tolerability to aromatic C-Br and C-Cl
Synlett, 507-507 (1993)
Ana I Ojeda-Amador et al.
Inorganic chemistry, 55(11), 5719-5728 (2016-05-14)
Reacting cesium fluoride with an equimolar n-hexane solution of lithium bis(trimethylsilyl)amide (LiHMDS) allows the isolation of CsHMDS (1) in 80% yield (after sublimation). This preparative route to 1 negates the need for pyrophoric Cs metal or organocesium reagents in its
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