Abstract
[131-62-4] C7H5IO3 (MW 264.02) InChI = 1S/C7H5IO3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4,10H InChIKey = AZJIXRYFAZOEMC-UHFFFAOYSA-N (cleavage of phosphates,2 oxygenation of α,β-unsaturated carbonyl compounds,3 α-hydroxylation of ketones,4 methoxylation of steroids,5 oxidation of sulfides,6 chemical cleavage of proteins,7 palladium-catalyzed coupling with arylboronic acids,8 preparation of iodonium salts,9 synthesis of benziodoxole derivatives10) Alternative Names: 2-iodosobenzoic acid; 2-iodosylbenzoic acid; o-iodosobenzoic acid; o-iodosylbenzoic acid; IBA [304-91-6]. Physical Data: mp 231–232 °C (dec). Solubility: soluble in H2O, DMSO, alcohol; insoluble in ether, CH2Cl2, MeCN, and nonpolar organic solvents. Form Supplied in: white microcrystalline solid; commercially available; typical impurities: 2-iodobenzoic acid and 2-iodoxybenzoic acid. Analysis of Reagent Purity: iodometric titration,11 elemental analysis, 1H NMR. Preparative Methods: oxidation of 2-iodobenzoic acid with fuming nitric acid at 50 °C12; chlorination of 2-iodobenzoic acid followed by hydrolysis with aq NaOH13; oxidation of 2-iodobenzoic acid with NaIO4 in boiling 30% aq acetic acid14; oxidation of 2-iodobenzoic acid with potassium persulfate in H2SO4 at 0 °C.14 Purification: dissolution in aq NaOH followed by acidification to pH 3 by addition of 5% aq acetic acid.11 Handling, Storage, and Precautions: can be stored indefinitely long in the dark; refrigeration should be used for long-term storage.
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