Lithium bis(trimethylsilyl)amide, 20% (ca 1.06M) soln. in THF/ethylbenzene, packaged in resealable septum cap bottle

Description

CAS: 4039-32-1 | C6H18LiNSi2 | 167.327 g/mol

Lithium bis(trimethylsilyl)amide is used in generating enolates for preparing lactone precursors, pyranones, and cyclohexanes. It is used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines and in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles. It is also used in the lithiation of ethyl acetate and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Lithium bis(trimethylsilyl)amide is used in generating enolates for preparing lactone precursors, pyranones, and cyclohexanes. It is used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines and in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles. It is also used in the lithiation of ethyl acetate and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones.

Solubility
Reacts with water.

Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Store under inert gas. Incompatible with oxidizing agents.

Specifications

Chemical Identifiers

• CAS: 4039-32-1
• Molecular Formula: C6H18LiNSi2
• Molecular Weight (g/mol): 167.327
• MDL Number: MFCD00008261
• InChI Key: YNESATAKKCNGOF-UHFFFAOYSA-N
• Synonym: lithium bis trimethylsilyl amide, lithium hexamethyldisilazide, lihmds, lhmds, hexamethyldisilazane lithium salt, unii-rc4n1i108m, lithiumbis trimethylsilyl amide, lithium bis trimethylsilyl azanide, lithium hexamethyldisilazane, lithium bis-trimethylsilyl amide
• PubChem CID: 2733832
• IUPAC Name: lithium;bis(trimethylsilyl)azanide
• SMILES: [Li+].C[Si](C)(C)[N-][Si](C)(C)C

• Quantity: 100 mL
• Linear Formula: [(CH₃)₃Si]₂NLi
• UN Number: UN2924
• Beilstein: 8136861
• Flash Point: −17°C (1°F)
• Solubility Information: Reacts with water.
• Formula Weight: 167.33
• Concentration or Composition (by Analyte or Components): 20% (≈1.06M) soln. in THF/ethylbenzene
• Sensitivity: Air and moisture sensitive
• Density: 0.891
• Chemical Name or Material: Lithium bis(trimethylsilyl)amide, packaged in resealable septum cap bottle

Safety and Handling

Hazard Category	H225-H302-H304-H314-H335-H336-H351
Hazard Statement	GHS H Statement H225-H314-H351-H335 Highly flammable liquid and vapor. Causes severe skin burns and eye damage. Suspected of causing cancer. May cause respiratory irritation.
Precautionary Statement	P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P281-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
DOTInformation	Transport Hazard Class: 3; Packing Group: II; Proper Shipping Name: FLAMMABLE LIQUIDS, CORROSIVE, N.O.S.
EINECSNumber	223-725-6
TSCA	Yes
Recommended Storage	Ambient temperatures; Store under Nitrogen

SDS

RUO – Research Use Only