High Quality Content by WIKIPEDIA articles! Sodium bis(trimethylsilyl)amide is the chemical compound with the formula ((CH3)3Si)2NNa. This species, usually called NaHMDS, is a strong base used for deprotonation reactions or base catalyzed reaction. Its advantages are that it is available as a solid and it is soluble in a wide range of nonpolar solvents by virtue of the lipophilic TMS groups. NaHMDS is quickly destroyed by water to form sodium hydroxide and bis amine. It is common that polar organometallic reagents are depicted as ions, when in fact such species are rarely ionic. The structure shown in the figure is a better representation - the sodium atom is attached to the nitrogen atom via a polar covalent bond.

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