Heptadecafluorooctyl[bis(trifluoroacetoxy)]iodine

Abstract

[77758-73-7] C12F23IO4 (MW 771.99) InChI = 1S/C12F23IO4/c13-3(14,15)1(37)39-36(40-2(38)4(16,17)18)12(34,35)10(29,30)8(25,26)6(21,22)5(19,20)7(23,24)9(27,28)11(31,32)33 InChIKey = BGOPEDHZDINAJF-UHFFFAOYSA-N (preparation of (perfluoroalkyl)aryliodonium salts,2 preparation of [hydroxy(sulfonyloxy)iodo]perfluoroalkanes,3 fluorous reagent for oxidation of 1,4-hydroquinones,4 fluorous reagent for oxidation of secondary alcohols5) Alternative Names: [bis(trifluoroacetoxy)iodo]heptadecafluorooctane, [bis(trifluoroacetoxy)iodo]perfluorooctane. Physical Data: mp 112–113.5 °C (dec).5 Solubility: highly soluble in DMSO, acetone, methanol, ether, and octafluorotoluene; moderately soluble in dichloromethane and chloroform.5 Form Supplied in: not available from commercial sources; prepared as white microcrystalline solid. Analysis of Reagent Purity: elemental analysis, 13C and 19F NMR.5 Preparative Methods: oxidation of the commercial perfluorooctyl iodide by using 80% hydrogen peroxide and trifluoroacetic anhydride followed by removal of volatile products in vacuum (yield 97–98%);3-5 a similar procedure using 30% hydrogen peroxide;2 oxidation of the commercial perfluoroalkyl iodide by using urea–hydrogen peroxide complex in a mixture of trifluoroacetic anhydride and trifluoroacetic acid at −5 to 0 °C (yield 94%).6 Purification: used without additional purification. Handling, Storage, and Precautions: can be stored for several weeks in a refrigerator in the absence of moisture.