4-Dimethylaminopyridine

Catalog Number:
001704

CAS Number:

1122-58-3
Molecular Formula:

C7H10N2

Molecular Weight:

122.17

MDL Number:

MFCD00006418

DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides4, the Baylis-Hillman reaction5, hydrosilylations, tritylation, the Steglich rearrangement and the Staudinger synthesis of β-lactams. Chiral DMAP analogues are used in kinetic resolution experiments of mainly secondary alcohols and Evans auxilary type amides. 1,2 DMAP is also used as a coupling agent for the synthesis of peptide and an efficient ligand for the Heck reaction in aqueous media 3.

Reference

  1. Höfle, G., Steglich, W., Vorbrüggen, H.. Angew. Chem. Int. Ed. Engl. 1978, 17, 569.
  2. Ryan P. Wurz . Chem. Rev. 2007, 107, 5570.
  3. D. V. Evdokimov, N. A. Bumagin. Russ. Chem. Bull. 2007, 56, 1093.
  4. Wilson, S.R.; Augelli, C.E. Org. Synth. 1990, 68, 210.
  5. Rezgui, F.; El Gaied, M. M. Tetrahedron Lett. 1998, 39, 5965.