4-(Dimethylamino)pyridine [CAS No. 1122-58-3]
Synonym(s): N,N-Dimethylpyridin-4-amine, DMAP
Empirical Formula (Hill Notation): C7H10N2
Assay: ≥99%
Form: chips; Crystalline powder flakes
MP: 108-110 °C (lit.)
Solubility: H2O: 50 mg/mL
Description
4-(Dimethylamino)pyridine (DMAP) is a highly versatile nucleophilic catalyst for acylation reactions and esterifications. It is also employed in various organic transformations like Baylis-Hillman reaction, Dakin-West reaction, protection of amines, C-acylations, silylations, applications in natural products chemistry, and many others.
Application
4-(Dimethylamino)pyridine can be used as a catalyst:
- To synthesize 3,5-disubstituted 2,6-dicyanoaniline by reacting malononitrile, aldehydes, and β-nitroolefins.
- For the acylation of alcohols with acid anhydrides under auxiliary base- and solvent-free conditions to synthesize corresponding esters.
- In Baylis-Hillman reaction to form carbon-carbon bond by the coupling of an activated alkene with an aldehyde or ketone.
A highly efficient catalyst for acylation reactions.


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