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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 ...
Lithium, sodium, and potassium bis(trimethylsilyl)amides are commercially available. When free of solvent, the lithium [5] and sodium [6] complexes are trimeric, and ...
Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula NaNH 2. It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white, but commercial samples are typically gray due to the presence of small quantities of ...
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.
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.
Developing an IUPAC name for bistriflimide that indicates the structure and reactivity is challenging, and changes to current names have been proposed. The main difficulty arises from the ambiguous use of the word amide to mean an acylated (including sulfonylated) amine or the anionic form of an amine.
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]
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).