324620

Lithium bis(trimethylsilyl)amide

97%

• Synonym(s): Hexamethyldisilazane lithium salt
• Linear Formula: [(CH₃)₃Si]₂NLi
• CAS Number: 4039-32-1
• Molecular Weight: 167.33
• EC Number: 223-725-6
• MDL number: MFCD00008261
• UNSPSC Code: 12352111
• PubChem Substance ID: 24859455
• NACRES: NA.22

Properties

• assay: 97%
• form: solid
• density: 0.860 g/mL at 25 °C (lit.)
• 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 a non-nucleophilic strong Brønsted base, which is generally soluble in most of the nonpolar organic solvents. It is most commonly employed in organic reactions.

Application

Base employed in generating enolates for the preparation of lactone precursors, pyranones, and cyclohexanes.
Used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines. Also used in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles.

Safety Information

• pictograms: GHS02,GHS05
• signalword: Danger
• hcodes: H228,H251,H314
• pcodes: P210 - P235 - P260 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B
• supp_hazards: EUH014
• Storage Class: 4.2 - Pyrophoric and self-heating hazardous materials
• wgk_germany: WGK 2
• flash_point_f: 62.6 °F - closed cup
• flash_point_c: 17 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges