DMAP

(4-Dimethylaminopyridine)

Other Names:

N,N-Dimethylpyridin-4-amine

General Information:

Structure:

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

Safety:

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

References:

1) Patent Reference: WO2010027500, page 105, (22.8 MB)

2) Patent Reference: WO2015144799, page 92, (18.8 MB)

3) Patent Reference: WO2015158653, page 27, (2.9 MB)

4) Patent Reference: WO2011017578, page 126, (8.3 MB)

5) Patent Reference: WO2016011390, page 459, (20.2 MB)

6) Patent Reference: WO2014149164, page 429, (23.7 MB)

7) Patent Reference: WO2015144799, page 250, (18.8 MB)

8) Wikipedia: 4-Dimethylaminopyridine (link)

9) www.sigmaaldrich.com: 4-(Dimethylamino)pyridine (link)

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