Sodium bis(trimethylsilyl)amide is the organosilicon compound with the formula NaN(Si(CH3)3)2.

[1] NaHMDS is quickly destroyed by water to form sodium hydroxide and bis(trimethylsilyl)amine.

Although the Na–N bond is polar covalent as a solid, when dissolved in nonpolar solvents this compound is trimeric, consisting of a central Na3N3 ring.

Typical reactions: NaHMDS deprotonates compounds containing weakly acidic O–H, S–H, and N–H bonds.

This method has been extended to aminomethylation via the reagent CH3OCH2N(Si(CH3)3)2, which contains a displaceable methoxy group CH3O–.