4-Dimethylaminopyridine



4-Dimethylaminopyridine
IUPAC name 4-Dimethylaminopyridine
Other names DMAP, 4-(Dimethylamino)-pyridine, N,N-Dimethyl-4-aminopyridin
Identifiers
CAS number 1122-58-3
SMILES CN(C)C1=CC=NC=C1
Properties
Molecular formula C7H10N2
Molar mass 122.17 g/mol
Melting point

110-113 °C

Boiling point

162 °C at 50 mmHg

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
DMAP redirects here. For the cyanide antidote see 4-Dimethylaminophenol

4-Dimethylaminopyridine (DMAP) is a nucleophilic catalyst which catalyzes a variety of reactions. For example Staudinger synthesis of β-lactams and many more.[1][2]

Esterification catalyst

In the case of triethylamine) deprotonates the protonated DMAP, reforming the catalyst. The reaction runs through the described nucleophilic reaction pathway irrespectively from the used anhydride.[3]

References

  1. ^ Catalysis by 4-dialkylaminopyridines Donald J Berry, Charles V Digiovanna, Stephanie S Metrick and Ramiah Murugan Arkivoc O-401R 2001 Online review
  2. ^ 4-Dialkylaminopyridines as Highly Active Acylation Catalysts Höfle, G., Steglich, W., Vorbrüggen, H. Angew. Chem. Int. Ed. Engl. 1978 , 17 , 569-583.
  3. ^ The DMAP-Catalyzed Acetylation of Alcohols - A Mechanistic Study (DMAP = 4-(dimethylamino) -pyridine) S. Xu, I. Held, B. Kempf, H. Mayr, W. Steglich, H. Zipse, Chem. Eur. J. 2005, 11, 4751 - 4757

Further reading

B. Neises, W. Steiglich, Organic Syntheses, Coll. Vol. 7, p.93 (1990); or Vol. 63, p.183 (1985).

 
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