CAS 4185-69-7, Cat. No EN300-45333
Reagent for synthesis of N-alkyl or N-aryl pyridinium salts, Zincke aldehydes
Zincke salt is a unique electrophilic reagent that enables the synthesis of pyridinium salts with primary amines. This compound presents as a white, stable solid, and it exhibits solubility primarily in protic solvents and other highly polar solutions. In cases where improved solubility in organic solvents is desired, solubility can be enhanced via anion exchange with a simple salt. The reaction involving electrophilic Zincke salts and nucleophilic primary alkyl- or arylamines leads to the formation of new pyridinium salts, accompanied by the expulsion of 2,4-dinitroaniline. In many instances, this chemical transformation can take place in a one-pot procedure, although certain protocols may require the isolation of intermediate acyclic imines, followed by subsequent heating with an acid or base to induce cyclization. The reaction with secondary amines facilitates the formation of Zincke aldehydes, which are important building blocks.
Synonyms: 1-(2,4-Dinitrophenyl)pyridinium chloride (6CI, 7CI); Pyridinium, 1-(2,4-dinitrophenyl)-, chloride (8CI, 9CI); (2,4-Dinitrophenyl)pyridinium chloride; 1-(2,4-Dinitrophenyl)-1λ5-pyridin-1-ylium chloride; 1-(2,4-Dinitrophenyl)pyridin-1-ium chloride; N-(2,4-Dinitrophenyl)pyridinium chloride