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/REAXYS Number: 3567910
• MDL number: MFCD00008261
• UNSPSC Code: 12352111
• 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:

• To catalyze polymerization reaction in the synthesis of poly(p-benzamide)s. [1]
• In the synthesis of cyclic poly(α-peptoid)s and α-(difluoromethyl)styrene. [2]
• In directed aldol condensations and Darzens condensation reactions; α-arylation of aryl ester derivatives and allylic amination reaction.
• 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,GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H225,H314,H335,H336,H351
• pcodes: 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 - STOT SE 3
• target_organs: Central nervous system, Respiratory system
• supp_hazards: EUH014,EUH019
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 2
• flash_point_f: 1.4 °F - closed cup
• flash_point_c: -17 °C - closed cup