766917

Lithium bis(trimethylsilyl)amide solution

1.5 M in THF

• Synonym(s): Hexamethyldisilazane lithium salt
• Linear Formula: [(CH₃)₃Si]₂NLi
• CAS Number: 4039-32-1
• Molecular Weight: 167.33
• Beilstein: 3567910
• MDL number: MFCD00008261
• UNSPSC Code: 12352111
• PubChem Substance ID: 329767270
• NACRES: NA.22

Properties

• form: liquid
• concentration: 1.5 M in THF
• density: 0.893 g/mL at 25 °C
• 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

Description

General description

Lithium bis(trimethylsilyl)amide is commonly used in organic synthesis as a non-nucleophilic strong Bronsted base. It is soluble in most nonpolar solvents such as aromatic hydrocarbons, hexanes, and THF.

Application

Lithium bis(trimethylsilyl)amide can be used as a reagent:     

• In the deprotonation and nucleophilic difluoromethylation reactions.
• 3-methoxy substituted dihydropyrrole derivatives by reacting with aldehydes and lithiated methoxyallene via in situ formations of N-trimethylsilylated imines.  
• In Darzens condensation and directed aldol condensation reactions.      
• To synthesize poly(N-octyl-p-benzamide)s by chain-growth polycondensation of 4-octylaminobenzoic acid methyl ester.

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H251,H314,H335,H336,H351
• Precautionary Statements: P210 - P235 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Self-heat. 1 - Skin Corr. 1B - STOT SE 3
• Target Organs: Central nervous system, Respiratory system
• Supplementary Hazards: EUH014,EUH019
• Storage Class Code: 4.2 - Pyrophoric and self-heating hazardous materials
• WGK: WGK 2
• Flash Point(F): 31.3 °F - closed cup
• Flash Point(C): -0.4 °C - closed cup