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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) 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) 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