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

2, 10, 25, 100, 100, 800 mL in Sure/Seal™

1 L in Sure/Seal™

8, 18, 18, 20, 100, 200 L

100 g

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 - 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
• Supplementary Hazards: EUH014 - EUH019
• Storage Class Code: 4.2 - Pyrophoric and self-heating hazardous materials
• WGK: WGK 2
• Flash Point(F): 1.4 °F - closed cup
• Flash Point(C): -17 °C - closed cup