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Lithium bis(trimethylsilyl)amide

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Lithium bis(trimethylsilyl)amide Basic information

Product Name:
Lithium bis(trimethylsilyl)amide
Synonyms:
  • 1,1,1,3,3,3-HEXAMETHYLDISILAZAN LITHIUMSALZ
  • 1,1,1,3,3,3-HEXAMETHYLDISILAZANE LITHIUM SALT
  • HEXAMETHYLDISILAZANE LITHIUM SALT
  • LHMDS
  • LIHMDS
  • LITHIUM HEXAMETHYLDISILAZANE
  • LITHIUM HEXAMETHYLDISILAZIDE
  • LITHIUM-BIS-(TRIMETHYLSILYL)-AMID
CAS:
4039-32-1
MF:
C6H18LiNSi2
MW:
167.33
EINECS:
223-725-6
Product Categories:
  • Classes of Metal Compounds
  • Li (Lithium) Compounds
  • Si (Classes of Silicon Compounds)
  • Silazanes
  • Silicon Compounds (for Synthesis)
  • Si-N Compounds
  • Synthetic Organic Chemistry
  • Typical Metal Compounds
Mol File:
4039-32-1.mol
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Lithium bis(trimethylsilyl)amide Chemical Properties

Melting point:
73°C
Boiling point:
55-56 °C
Density 
0.860 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.425(lit.)
Flash point:
48 °F
storage temp. 
Store below +30°C.
solubility 
hydrolysis
form 
Powder
color 
White
Specific Gravity
0.891
Specific Gravity
0.716
Water Solubility 
hydrolysis
Sensitive 
Air & Moisture Sensitive
Hydrolytic Sensitivity
8: reacts rapidly with moisture, water, protic solvents
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
BRN 
3567910
InChIKey
YNESATAKKCNGOF-UHFFFAOYSA-N
CAS DataBase Reference
4039-32-1(CAS DataBase Reference)
EPA Substance Registry System
Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, lithium salt (4039-32-1)
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Safety Information

Hazard Codes 
F,C,N
Risk Statements 
11-34-48/20-63-65-67-51/53-35-20-62-14-40-37-19
Safety Statements 
9-16-26-29-33-36/37/39-45-61-62-57-43
RIDADR 
UN 2925 4.1/PG 2
WGK Germany 
3
10-23
TSCA 
Yes
HazardClass 
4.3
PackingGroup 
II
HS Code 
29319090

MSDS

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Lithium bis(trimethylsilyl)amide Usage And Synthesis

Chemical Properties

light yellow to yellow crystalline powder

Physical properties

distillable low-melting solid; mp 70–72 °C, bp 115 °C/1mmHg. LHMDS is a cyclic trimer in the solid state,3 whereas in benzene solution it exists in a monomer–dimer equilibrium. LHMDS exists as a tetramer-dimer mixture in hydrocarbons and as a dimer-monomer mixture in THF and ether. Treatment of LHMDS with trialkylamines increases the monomer concentration, whereas the use of diamines affords exclusively the corresponding chelated monomer. LHMDS is less soluble, less basic, more stable, and much less sensitive to air compared to lithium diisopropylamide. pKa 29.5 (THF, 27 °C).

Uses

Lithium bis(trimethylsilyl)amide is used as nonnucleophilic base to generate kinetic ketone and ester enolates. It is considerably more selective than LDA and undesired reductions (e.g., of nonenolizable ketones observed in the case of LDA) can be avoided by using LHMDS.

Uses

Lithium Hexamethyldisilazide is widely used as strong nonnucleophilic base

Uses

Lithium bis(trimethylsilyl)amide is a base used in preparation of dienes and enolates. It is used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines. Lithium bis(trimethylsilyl)amide is also used in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles.

Preparation

It is conveniently prepared by the reaction of hexamethyldisilazane with n-butyllithium in hexane. For most uses the hexane is then evaporated and replaced with THF.

General Description

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Lithium bis(trimethylsilyl)amide Preparation Products And Raw materials

Preparation Products

Raw materials

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