Lithium bis(trimethylsilyl)amide, CAS No. 4039-32-1

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4039-32-1

Catalog No. EBD7289

CAS 4039-32-1

Name Lithium bis(trimethylsilyl)amide

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Basic Information

Synonyms: 1,1,1,3,3,3-Hexamethyldisilazanelithiumsalt Lithiumhexamethyldisilazide Lithiumbis(trimethylsilyl)amide lithium1,1,1,3,3,3-hexamethyldisilazan-2-ide silanamine,1,1,1-trimethyl-N-(trimethylsilyl)-,lithiumsalt(1:1) LiHMDS

Molecular Formula: C6H18LiNSi2

Molecular Weight: 167.33

MDL Number: MFCD00008261

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Other Basic Synthetic Reagents Synthetic Chemistry > Organometallic Reagents > Other Organometallic Reagents

Product Description:

Lithium bis(trimethylsilyl)amide (LiHMDS, CAS 4039-32-1) is a sterically hindered, non-nucleophilic strong base with the formula [(CH₃)₃Si]₂NLi. It is commercially available as a solid or as solutions in various organic solvents such as tetrahydrofuran (THF) or hexane. Its structure features a lithium cation coordinated by the amide nitrogen, which is flanked by two bulky trimethylsilyl groups. Its primary application is as a deprotonating agent in organic synthesis. The steric bulk of the trimethylsilyl groups prevents nucleophilic attack, making LiHMDS highly selective for proton abstraction over addition reactions. It is extensively used for the generation of enolates from carbonyl compounds (especially esters and ketones), for metallation reactions, and in a wide range of base-catalyzed transformations, including aldol condensations, Claisen condensations, and Michael additions. It is a cornerstone reagent in modern synthetic methodology. LiHMDS is moisture- and air-sensitive, requiring handling under inert atmosphere (argon or nitrogen). It is a crucial reagent in the synthesis of pharmaceuticals, agrochemicals, and complex natural products, where its predictable and clean reactivity is highly valued.

Physical Properties

Melting Point: 73°C

Boiling Point: 55-56 °C

Flash Point: 17 °C

Density: 0.860 g/mL at 25 °C(lit.)

Solubility: hydrolysis

Refractivity: n20/D 1.425(lit.)

Storage: below 5°C

Safety Information

Packing Level: II

Hazard Category: 8(4.1)

Transport Codes: 2925

Analytical Data

Appearance: light yellow to yellow crystalline powder