4-Dimethylaminopyridine

<p>4-Dimethylaminopyridine (DMAP) is a derivative of <a href="/facts/Pyridine/X817hCch">pyridine</a> with the <a href="/facts/Chemical_formula/hghUtthl">chemical formula</a> (CH3)2NC5H4N.  This white solid is of interest because it is more basic than <a href="/facts/Pyridine/X817hCch">pyridine</a>, owing to the <a href="/facts/Resonance_(chemistry)/5tymwoIP">resonance stabilisation</a> from the NMe2 substituent.
</p><p>Because of its basicity, DMAP is a useful nucleophilic <a href="/facts/Catalyst/LPBS7TQC">catalyst</a> for a variety of reactions such as <a href="/facts/Esterification/FoUAIIw4">esterifications</a> with <a href="/facts/Anhydride/9YnWCsJo">anhydrides</a>, the <a href="/facts/Baylis-Hillman_reaction/F8hfP4tR">Baylis-Hillman reaction</a>, <a href="/facts/Hydrosilylation/dPqlRe0t">hydrosilylations</a>, tritylation, the Steglich rearrangement, <a href="/facts/Staudinger_synthesis/R59prR0B">Staudinger synthesis</a> of β-lactams and many more. Chiral DMAP analogues are used in <a href="/facts/Kinetic_resolution/ac0BKEq0">kinetic resolution</a> experiments of mainly secondary alcohols and Evans auxiliary type amides.
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4-Dimethylaminopyridine open-in-new

4-Dimethylaminopyridine