4-Dimethylaminopyridine

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4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This white solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation of the conjugate acid from the NMe2 substituent. Because of its basicity, DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement, Staudinger synthesis of β-lactams and many more. DMAP analogues are used in kinetic resolution experiments of mainly secondary alcohols and Evans auxiliary type amides.

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