225770

Lithium bis(trimethylsilyl)amide solution

1.0 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
• PubChem Substance ID: 24853520
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 200
• concentration: 1.0 M in THF
• density: 0.891 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 (LHMDS) is a non-nucleophilic strong base widely used in organic synthesis for deprotonation reactions and base-catalyzed reactions. It is generally soluble in most nonpolar organic solvents.

Application

Lithium bis(trimethylsilyl)amide solution (1.0 M in THF) can be used as a base in directed aldol condensations and Darzens condensation reactions; α-arylation of aryl ester derivatives and allylic amination reaction. LHMDS is a preferred base for the generation of kinetic enolates than sodium hexamethyldisilazide (NaHMDS) because the enolates produced are more regiostable than those produced with NaHMDS.

Packaging

The 25 mL Sure/Seal^™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

View returnable container options.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Safety Information

• Pictograms: GHS02,GHS05,GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H225 - H314 - H335 - H336 - H351
• Precautionary Statements: P202 - P210 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B
• Supplementary Hazards: EUH014 - EUH019
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 2
• Flash Point(F): 1.4 °F - closed cup
• Flash Point(C): -17 °C - closed cup