Title: DMAP
CAS Registry Number: 1122-58-3
CAS Name: N,N-Dimethyl-4-pyridinamine
Synonyms: 4-(dimethylamino)pyridine
Molecular Formula: C7H10N2
Molecular Weight: 122.17
Percent Composition: C 68.82%, H 8.25%, N 22.93%
Literature 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?fle
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.
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.
Melting point: mp 112-113°
pKa: pKa (20°): 9.7
Use: In a wide variety of organic syntheses as a catalyst.
