1-(2,4-Dinitrophenyl)pyridinium Chloride

Abstract

[4185-69-7] C11H8ClN3O4 (MW 81.65) InChI = 1S/C11H8N3O4.ClH/c15-13(16)9-4-5-10(11(8-9)14(17)18)12-6-2-1-3-7-12;/h1-8H;1H/q+1;/p-1 InChIKey = UYHMQTNGMUDVIY-UHFFFAOYSA-M (reagent for synthesis of N-alkyl or N-aryl pyridinium salts1, 2; can undergo ring opening to form 5-amino- or 5-hydroxy-2,4-pentadienal derivatives3, 4) Alternate Name: Zincke salt. Physical Data: mp 199–202 °C. Solubility: sol H2O, DMSO; moderately sol alcohol solvents; insol acetone, CH2Cl2, diethyl ether, petroleum ether. Form Supplied in: white solid. Analysis of Reagent Purity: NMR in DMSO-d6. Preparative Methods: the title reagent can be prepared by reaction of pyridine and 2,4-dinitrochlorobenzene in acetone, and collected by filtration. Purification: recrystallization from ethanol. Handling, Storage, and Precautions: the title reagent is relatively safe, being stable indefinitely as a solid, but should be stored in a cool, dry location away from light. 2,4-Dinitroaniline is a by-product in many reactions involving the title reagent, and is known to be toxic via inhalation, skin contact, and ingestion.