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General Information:


CAS Number: 1122-58-3

Molecular Weight: 122.17 g/mol

Appearance: White solid

Melting Point: 108-110 C

4-Dimethylaminopyridine (DMAP) is a nucleophilic catalyst used for numerous different reactions. DMAP is a very effective acyl transfer agent. The use of 4-aminopyridines (such a DMAP) has been shown to speed up the esterification of hindered alcohols via acid anhydrides by up to 10,000 fold.

Common Uses:

Nucleophilic catalyst for Boc protections

Reagent for amide couplings (EDC + DMAP)

Reagent for the conversion of carboxylic acids to esters (Steglich Esterification)

Nucleophilic catalyst for TBS protections (silylation)

Nucleophilic catalyst for the conversion of alcohols to triflates


4-Dimethylaminopyridine (DMAP) is considered to be highly toxic. The fact that DMAP is readily absorbed through the skin makes it even more dangerous.


1) WO2010027500, page 105

2) WO2015144799, page 92

3) WO2015158653, page 27

4) WO2011017578, page 126

5) WO2016011390, page 459

6) WO2014149164, page 429

7) WO2015144799, page 250

8) Wikipedia: 4-Dimethylaminopyridine (link)

9) 4-(Dimethylamino)pyridine (link)

10) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis, Activating Agents and Protecting Groups