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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.
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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]
Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula MeC(OSiMe 3)NSiMe 3 (Me = CH 3). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with moisture and solvents containing OH and NH groups .
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).