A novel system for catalytic oxidation of phenol and chlorophenol pollutant in water by tetranitro iron (II) phthalocyanine (TNFe(II)Pc) is reported for the first time. In this system, several phenolic substrates (phenol, 2-chlorophenol, 4-chlorophenol and 2,4-dichlorophenol) could be easily oxidized by naturally dissolved oxygen in the presence of INFe(II)Pc, and then rapidly combined with 4-aminoantipyrine to generate the pink dye. The catalytic oxidation process and resulting products were monitored by UV-Vis spectroscopy and high performance liquid chromatography-mass spectrometer (HPLC-MS) technique. Control experiments demonstrated that the generation of superoxide anion radical was crucial for the dye formation, and a possible mechanism involved a successive single electron transfer from phenolic substrates to O(2) via the axis of TNFe(II)Pc was proposed. Potentially, this system is promising for application in chromogenic identification of phenolic pollutant. Crown Copyright (C) 2011 Published by Elsevier B.V. All rights reserved.