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• W2184920592 abstract "[61717-82-6] C7H5IO4 (MW 280.02)InChI = 1S/C7H5IO4/c9-7-5-3-1-2-4-6(5)8(10,11)12-7/h1-4H,(H,10,11)InChIKey = CQMJEZQEVXQEJB-UHFFFAOYSA-N(mild oxidant for alcohols and closely related systems1-5 with wide functional group tolerance; dehydrogenation agent for aldehydes and ketones to give enals or enones, respectively;6-8 oxidant for silyl enol ethers to generate the corresponding enone;9 reagent to effect benzylic oxidation;7, 10 single electron transfer agent for mediating cyclization of unsaturated N-aryl amides, (thio)carbamates, and ureas;11-13 versatile reagent for cleavage of oximes,14 tosylhydrazones,14 and triethylsilyl ethers15)Alternate Name: o-iodoxybenzoic acid, o-iodylbenzoic acid.Physical Data: white crystalline solid, mp 233 °C (dec).Solubility: soluble in DMSO.Analysis of Reagent Purity: 1H NMR (500 MHz, d6-DMSO): δ 8.40 (very broad singlet, 1H), 8.13 (d, J = 7.9 Hz, 1H), 8.02 (d, J = 7.5 Hz, 1H), 7.99 (t, J = 7.6 Hz, 1H), 7.83 (t, J = 7.4 Hz, 1H).Preparative Methods: older methods used to oxidize 2-iodobenzoic acid to IBX using potassium permanganate,16a potassium bromate,16b or chlorine16c have been shown to contaminate the product with dangerous residues,17, 18 and have largely been surpassed by an environment friendly method using OXONETM (2KHSO5–KHSO4–K2SO4, 1.3 equiv) in water at 73 °C, which precipitates high purity crystalline IBX after 3 h. For the best result, the crystalline material should be washed with both water and acetone.18Purification: wash solid with water followed by acetone and dry in a darkened vessel under vacuum. It should be noted that recrystallization from water tends to reduce the purity of IBX and the quality of samples can be confirmed readily by NMR spectroscopy (refer to the section ‘Analysis of Reagent Purity’).Handling, Storage, and Precautions: IBX is reported to be explosive under impact or heating to > 200 °C.17, 19 To help prevent decomposition, dry well, store in darkened vessel in a nitrogen atmosphere and refrigerate. Under these conditions, IBX is > 95% pure after 6 months. IBX is considerably less sensitive to air and moisture than its derivative Dess-Martin periodinane ‘DMP, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one’. IBX decomposes when exposed to light. Work-up procedures to remove excess IBX and residual iodosobenzoic acid (IBA, the by-product resulting from the reduction of IBX) are operationally simple with the recommended procedure being dilution of the DMSO solution with an equal volume of 5% aqueous sodium bicarbonate (or saturated aqueous sodium thiosulfate) followed by extraction with diethyl ether (or another solvent suitable for the substrate). The organic phase should be washed with saturated aqueous sodium bicarbonate, water, and brine. The solvent can then be removed under reduced pressure, after drying with magnesium sulfate, to afford the crude product." @default.
• W2184920592 created "2016-06-24" @default.
• W2184920592 creator A5051379973 @default.
• W2184920592 creator A5061232778 @default.
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• W2184920592 creator A5083437792 @default.
• W2184920592 creator A5083726075 @default.
• W2184920592 date "2012-09-14" @default.
• W2184920592 modified "2023-10-05" @default.
• W2184920592 title "1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide" @default.
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