Sodium Bis(trimethylsilyl)amide (NaHMDS) CAS 1070-89-9 (2M soln. in THF)

Sodium Bis(trimethylsilyl)amide (NaHMDS) (CAS: 1070-89-9) (2M soln. in THF) is a strong base used in organic synthesis for deprotonation reactions and base catalyzed reaction.
NaHMDS was first prepared in 1958 by Wittig and Krebs through the reaction of sodium amide and trimethylsilyl chloride. Since then, NaHMDS has been widely used in organic synthesis reactions due to its strong basicity and ability to deprotonate weak acids.
NaHMDS is a strong base; deprotonates ketones and esters to generate enolate derivative. NaHMDS is a synthetically useful reagent in that it combines both high basicity and nucleophilicity, each of which may be exploited for useful organic transformations such as selective formation of enolates, preparation of Wittig reagents, formation of acyl anion equivalents, and the generation of carbenoid species. As a nucleophile, NaHMDS has been used as a nitrogen source for the preparation of primary amines. NaHMDS is useful as a sterically hindered base and as a nucleophile.
NaHMDS is a highly reactive base with a pKa value of approximately 25. NaHMDS is soluble in several types of organic solvents, such as tetrahydrofuran, diethyl ether, and toluene, but is insoluble in water. Its reactivity is due to the presence of a bulky trimethylsilyl group attached to the amide nitrogen, which makes the negatively charged nitrogen ion more accessible for reactions.
NaHMDS can be used in the preparation of new pharmaceuticals, agrochemicals, and materials for various applications.