577928

Lithium bis(trimethylsilyl)amide solution

1 M in toluene

• Synonym(s): LiHMDS, Hexamethyldisilazane lithium salt
• Linear Formula: [(CH₃)₃Si]₂NLi
• CAS Number: 4039-32-1
• Molecular Weight: 167.33
• Beilstein: 3567910
• MDL number: MFCD00008261
• UNSPSC Code: 12352111
• PubChem Substance ID: 24880899
• NACRES: NA.22

Properties

• Quality Level: 200
• concentration: 1 M in toluene
• density: 0.860 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 solution (LiHMDS) is generally used in organic synthesis as a non-nucleophilic strong Bronsted base.[1]

Application

LiHMDS can be used as a reagent:

• In the deprotonation and nucleophilic difluoromethylation reactions.[2][3]
• To synthesize isoquinoline derivatives by the addition of N-iodosuccinimide (NIS) to the α-benzyl tosylmethyl isocyanides.[4]
• To prepare arylboronic acid pinacol esters by the reaction of aryl fluorides with bis(pinacolato)diboron via palladium-catalyzed cross-coupling reaction.[5]

Lithium bis(trimethylsilyl)amide is generally used in organic synthesis as a non-nucleophilic strong Brønsted base. It can be used for salt metathesis reaction for the synthesis of cesium bis(trimethylsilyl)amide (CsHMDS) and lithium fluoride by reacting with cesium fluoride.[6]

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H251,H304,H314,H336,H361d,H373,H412
• Precautionary Statements: P210 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Self-heat. 1 - Skin Corr. 1B - STOT RE 2 - STOT SE 3
• Target Organs: Central nervous system
• Supplementary Hazards: EUH014
• Storage Class Code: 4.2 - Pyrophoric and self-heating hazardous materials
• WGK: WGK 3
• Flash Point(F): 48.0 °F - closed cup
• Flash Point(C): 8.9 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves