3389. DMAP

Nomenclature

CAS number: 1122-58-3
N,N-Dimethyl-4-pyridinamine; 4-(dimethylamino)pyridine.
C7H10N2; mol wt 122.17.
C 68.82%, H 8.25%, N 22.93%.

Description and references

Basic nucleophilic catalyst. Prepn: E. Koenigs et al., Ber. 58, 2571 (1925). Fluorescence spectra: S. Mishina et al., J. Photochem. Photobiol. A 141, 153 (2001). Use in Baylis-Hillman chemistry: K. Y. Lee et al., Bull. Korean Chem. Soc. 23, 659 (2002); in olefin hydroxylations: Q. Yao, Org. Lett. 4, 2197 (2002); in regioselective acylations: T. Kurahashi et al., Tetrahedron 58, 8669 (2002). Review of early literature and use in acylation chemistry: G. H"ofle et al., Angew. Chem. Int. Ed. 17, 569-583 (1978); U. Ragnarsson, L. Grehn, Acc. Chem. Res. 31, 494-501 (1998); and of alkylation: E. F. V. Scriven, Chem. Soc. Rev. 12, 129-161 (1983). Brief description and synthetic uses: A. Hassner, "4-(Dimethylamino)pyridine" in Encyclopedia of Reagents for Organic Synthesis 3, L. A. Paquette, Ed. (John Wiley & Sons, New York, 1995) pp 2022-2023.

Chemical structure

Properties

Colorless crystalline solid, mp 112-113°. pKa (20°): 9.70. Dipole moment (25°): 4.31 (benzene). Very sol in methanol, ethyl acetate, chloroform, methylene chloride, 1,2-dichloroethane, acetone and acetic acid; less sol in cold hexane, cyclohexane and water.

Use

In a wide variety of organic syntheses as a catalyst.