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324620

Sigma-Aldrich

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

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.

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Tetrahedron, 50, 9061-9061 (1994)
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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