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324620

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide

97%

Synonym(s):
Hexamethyldisilazane lithium salt
Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

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.

Packaging

10, 50, 250 g in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard 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 Germany

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

Certificate of Analysis

Certificate of Origin

Synlett, 507-507 (1993)
Tetrahedron Letters, 47, 8285-8285 (2006)
Lithium Bis(trimethylsilyl)amide and Tris(trimethylsilyl)amine
Inorganic Syntheses (1966)
The Journal of Organic Chemistry, 58, 7304-7304 (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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