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Merck
CN

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:
4039-32-1
Molecular Weight:
167.33
NACRES:
NA.22
PubChem Substance ID:
24859455
UNSPSC Code:
12352111
EC Number:
223-725-6
MDL number:
MFCD00008261

Key Documents

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Product Name

Lithium bis(trimethylsilyl)amide, 97%

InChI key

YNESATAKKCNGOF-UHFFFAOYSA-N

InChI

1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1

SMILES string

[Li]N([Si](C)(C)C)[Si](C)(C)C

assay

97%

form

solid

bp

110-115 °C (at 1.33 hPa)

mp

70-71 °C

density

0.860 g/mL at 25 °C (lit.)

Quality Level

200

pH

(12.4 at 23.7 °C)

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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.

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.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS7097
SHBS7094
SHBS6934
SHBS7095
SHBS7096

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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
Lithium Bis(trimethylsilyl)amide and Tris(trimethylsilyl)amine
Inorganic Syntheses (1966)
Synlett, 507-507 (1993)
Tetrahedron Letters, 47, 8285-8285 (2006)
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