Bis(dimethylamino)methane is the organic compound with the formula [(CH3)2N]2CH2. 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 (CH3)2NH + CH2O → [(CH3)2N]2CH2 + H2O
It is used for the dimethylaminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid: [(CH3)2N]2CH2 + H+ → (CH3)2NCH2+ + (CH3)2NH
Bis(dimethylamino)methane, being a Lewis base, functions as a bidentate ligand.
Related reagents N,N,N′,N′-Tetramethylformamidinium chloride Eschenmoser's salt is used for similar applications.
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