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This species, usually called NaHMDS (sodium hexamethyldisilazide), is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether , but also in aromatic solvents, like benzene and toluene by virtue ...
Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH 3) 3 Si] 2 NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms.
Lithium, sodium, and potassium bis(trimethylsilyl)amides are commercially available. When free of solvent, the lithium [5] and sodium [6] complexes are trimeric, and ...
The methylsilyl groups give KHMDS good solubility in most organic solvents. Solution structures are either solvated monomers or dimers (or mixtures thereof) with this depending on the coordinating power, concentration, and temperature of the solvent. [3]
LiHMDS is often used in organic chemistry as a strong non-nucleophilic base. [3] Its conjugate acid has a pK a of ~26, [4] making it is less basic than other lithium bases, such as LDA (pK a of conjugate acid ~36).
Sodium amide (also known as sodamide) is synthesized from sodium metal and ammonia with ferric nitrate catalyst. [3] [4] The sodium compound is white, but the presence of metallic iron turns the commercial material gray. 2 Na + 2 NH 3 → 2 NaNH 2 + H 2. Lithium diisopropylamide is a popular non-nucleophilic base used in organic synthesis.
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Tris(trimethylsilyl)amine is obtained by reaction of the sodium salt of hexamethyldisilazane - from hexamethyldisilazane and sodium amide [7] or from hexamethyldisilazane, sodium and styrene [1] - with trimethylchlorosilane in 80% yield. [8]