Sodium bis(trimethylsilyl)amide Sodium bisamide is the organosilicon compound with the formula 2 NNa. This species, usually called NaHMDS, 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 of the lipophilic TMS groups . NaHMDS is quickly destroyed by water to form sodium hydroxide and bisamine.Structure Although the N-Na bond is polar covalent as a solid, when dissolved in nonpolar solvents this compound is trimeric, consisting of a central Na3 N3 ring.Applications in synthesis NaHMDS is used as a base in organic synthesis . Typical reactions: NaHMDS is also used as a base to deprotonate other compounds containing weakly acidic O-H, S-H , and N-H bonds . These include cyanohydrins and thiols . NaHMDS is reagent to convert alkyl halides to amines in a two step process that begins with N-alkylation followed by hydrolysis of the N-Si bonds. This method has been extended to aminomethylation via the reagent 2 NCH2 OMe, which contains a displaceable methoxy group .
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