Lithium bis(trimethylsilyl)amide

Basic Information

View in Editor

CAS Number

4039-32-1

Molecular Formula

C6H18LiNSi2

Molecular Weight

167.4 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Hydrocarbons

Basic Physical Properties

Melting Point

73°C

Boiling Point

55-56 °C

Solubility

hydrolysis

Refractive Index

n20/D 1.425(lit.)

SMILES

View in Editor

[Li+].C[Si](C)(C)[N-][Si](C)(C)C

InChI

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

InChIKey

YNESATAKKCNGOF-UHFFFAOYSA-N

LogP

2.42250

Complexity

80.9

Safety Information

View Safety Information

GHS Hazard Pictograms

H228

H314

Hazard Statement

H228 Flammable solid
Flammable solids

H314 Causes severe skin burns and eye damage
Skin corrosion/irritation

Hazard Class

Class 4.3 Class 4.3

Sensitiveness

Air & Moisture Sensitive

Synonyms & References

English

Lithium Hexamethyldisilazide
lithium bis (trimethylsilyl)amide
lithium bis-trimethysilylamide
Hexamethyldisilazane lithium salt 1.25M (23-25%) in THF
Lithium hexamethyldisilazane
Lithium hexamethydisilazide
lithium bis(tri-methylsilyl)amide
lithium bis(trimethylsilyl) azanide
(HEXAMETHYLDISILAZANE)LITHIUM
J-802235
EC 223-725-6
lithium;bis(trimethylsilyl)azanide
Q219037
J-640310
FT-0605921
lithiohexamethyldisilazane
NSC 252161
LHMDS
DTXSID2044426
lithium N,N-bistrimethylsilylamide
lithiumbistrimethylsilyl amide
Lithium bis(trimethylsilyl)amide, 1M in Toluene
LiN(TMS)2
SCHEMBL6240
EINECS 223-725-6
A825085
lithium bis-(trimethylsilyl)-amide
Lithium bis(trimethylsilyl)amide, 20%, ca 1.06M in THF/EB
lithium bis(trimethyl silyl)amide
MFCD00008261
Lithium bis(trimethylsilyl)amide, 0.9-1.1M in hexane, packaged in resealable ChemSeal bottles

MDL Number

MFCD00008261

Customs Code

2931900090

FAQ

What is Lithium bis(trimethylsilyl)amide (CAS: 4039-32-1)?

Lithium bis(trimethylsilyl)amide is an organolithium compound with the chemical formula LiN(SiMe3)2. It is a strong nucleophile and base, commonly used in organic synthesis. The compound is typically a white solid or liquid, depending on its form, and is highly reactive with moisture and air. Its structure features two trimethylsilyl groups attached to a lithium-amide framework, making it effective for deprotonating acidic protons in various reactions.

What are the main uses of Lithium bis(trimethylsilyl)amide (CAS: 4039-32-1)?

Lithium bis(trimethylsilyl)amide is widely utilized in pharmaceuticals for synthesizing complex molecules, in industry for polymer production, and in research for coupling reactions like Sonogashira and Suzuki. It serves as a key reagent in organometallic chemistry, aiding in the formation of alkynes and other functional groups. Its applications also extend to the preparation of organolithium compounds and as a catalyst in specific chemical processes.

Is Lithium bis(trimethylsilyl)amide (CAS: 4039-32-1) safe?

Lithium bis(trimethylsilyl)amide is not classified as highly toxic, but it requires careful handling due to its reactivity with moisture and air. Safety measures include wearing protective gear like gloves and goggles, and working in a well-ventilated area. It may cause skin and eye irritation, so adherence to safety standards and proper storage is essential to minimize risks during use.

How should Lithium bis(trimethylsilyl)amide (CAS: 4039-32-1) be stored?

Lithium bis(trimethylsilyl)amide should be stored in a dry, cool environment (below 25°C), in airtight containers to prevent exposure to moisture and air. It is stable under inert atmosphere conditions and requires low humidity storage. Avoid light exposure and ensure containers are sealed properly to maintain its chemical integrity and safety.