Abstract [536-80-1] C6H5IO (MW 220.01) InChI = 1S/C6H5IO/c8-7-6-4-2-1-3-5-6/h1-5H InChIKey = JYJVVHFRSFVEJM-UHFFFAOYSA-N (oxygen atom transfer to ketones, metal-catalyzed oxygen atom transfer to alkenes, formation of alpha-diketones, bridgehead triflates, alpha,alpha,beta-unstaturated lactones and ketones, alpha-hydroxy-methyl acetals, alpha-keto triflates, alpha-hydroxy ketones, C-C coupling, oxidation of amines, azidation, metal-catalyzed alkene aziridination and difunctionalization, C-H amination, imination of sulfides and sulfoxides, carbene transfer, metal-free C-N bond forming reaction)
Alternate Name: iodosobenzene. Physical Data: mp 210 °C with decomposition (explodes); polymeric. Solubility: slightly soluble in H2O, MeOH. In MeOH the reagent is PhI(OMe)2. Both solvents, as well as CH2Cl2, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), 2,2,2-trifluoroethanol (TFE) and MeCN, are used for reactions. Form Supplied in: white to slightly yellow solid from synthesis. Preparative Methods: prepared as a white solid by base hydrolysis of commercially available (Diacetoxyiodo)benzene in 75% yield. Purifications: washing the solid with CHCl3 to remove traces of PhI. The material is obtained in about 99{%} purity as determined iodometrically. Caution should be taken when drying PhIO to remove traces of solvent: this must be made at room temperature under vacuum. 3g of PhIO have been reported to explode upon drying over toluene (110 °C, 0.1 torr). Handling, Storage, and Precautions: refrigeration should be used for long-term storage, since extended storage at room temperature leads to disproportionation of PhIO thereby producing a mixture of PhI and the explosive PhIO2.


Type de publication
Book Chapter
Année de publication
Book Title
Encyclopedia of Reagents for Organic Synthesis
American Cancer Society
Soumis le 25 septembre 2018