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Category: Synthesis
Posted on: July 6, 2007 8:23 PM, by Molecule of the Day
Dimethylaminopyridine, or DMAP, finds general use in organic synthesis as a "nucleophilic catalyst." Its strongly donating dimethylamine group affords it substantial nucleophilicity.
The adducts formed by its nucleophilic addition, however, are quite reactive - analogous to an acid chloride - so DMAP can push a reaction along nicely. See the Wikipedia entry for an example mechanism.
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Comments
DMAP is one of the better nucleophilic catalysts - it's cheap, readily available, and works. Perhaps the one disadvantage is that it can show up on TLC plates under the UV, so it's best to use a standard dilute solution of DMAP if you're tracking the progress of an unknown reaction.
Posted by: Tiling Paul | July 12, 2007 5:59 PM