P-Nitroperbenzoic acid

Abstract

[943-39-5] C7H5NO5 (MW 183.13) InChI = 1S/C7H5NO5/c9-7(13-12)5-1-3-6(4-2-5)8(10)11/h1-4,12H InChIKey = ZJAFQAPHWPSKRZ-UHFFFAOYSA-N (electrophilic reagent which delivers oxygen to alkenes2) Alternate Names: p-nitroperoxybenzoic acid; PNPBA. Physical Data: white crystalline solid; mp 136–137 °C. Solubility: sol THF, ether, CHCl3, benzene. Form Supplied in: white powder, 80% purity. Analysis of Reagent Purity: iodometric titration. Preparative Method: the reaction between Na2O2 and p-Nitrobenzoyl Chloride in THF in the presence of small quantities of water below −5 °C furnishes the sodium salt of PNPBA. p,p′-Dinitrobenzoyl peroxide and p-nitrobenzoic acid are removed from the reaction mixture during workup. PNPBA (purity 94–96%) is obtained in 85% yield (0.1 mol scale).2 Purification: recrystallization from ether–petroleum ether. Handling, Storage, and Precautions: at room temperature, PNPBA is stable for long periods. It should be stored in polyethylene containers in a refrigerator. Since PNPBA is a peroxide and potentially explosive, care should be exercised when carrying out reactions with it; during workup, check for the presence of peroxide before evaporating solvent.