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Bis(dimethylamino)methane

Bis(dimethylamino)methane is the organic compound with the formula [(CH<sub>3</sub>)<sub>2</sub>N]<sub>2</sub>CH<sub>2</sub>. It is classified as an aminal as well as a ditertiary amine, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reaction of dimethylamine and formaldehyde:

2 (CH<sub>3</sub>)<sub>2</sub>NH + CH<sub>2</sub>O → [(CH<sub>3</sub>)<sub>2</sub>N]<sub>2</sub>CH<sub>2</sub> + H<sub>2</sub>O

It is used for the dimethylaminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:

[(CH<sub>3</sub>)<sub>2</sub>N]<sub>2</sub>CH<sub>2</sub> + H<sup>+</sup> → (CH<sub>3</sub>)<sub>2</sub>NCH<sub>2</sub><sup>+</sup> + (CH<sub>3</sub>)<sub>2</sub>NH

Bis(dimethylamino)methane, being a Lewis base, functions as a bidentate ligand.

Related reagents

References