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• W1904874611 abstract "[64297-64-9] C7H5IO4 (MW 280.01)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[61717-82-6] C7H5IO4 (MW 280.01)InChI = 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(oxidizing agent used for dehydrogenation and oxygenation reactions)Physical Data: mp 250 °C (decomposition).Solubility: insoluble in water and most organic solvents, around 20% w/w in DMSO at 30 °C.Form Supplied in: white-powder formulation composed of a mixture of benzoic acid (23%), isophthalic acid (30%), and 2-iodoxybenzoic acid itself (47%).Preparative Method: 2-iodobenzoic acid (280 g), isophthalic acid (187 g), and benzoic acid (151 g) are mixed with Oxone® (1014 g) and water (4.6 L). After 2 h at 70 °C, the heterogeneous medium is cooled down to ambient temperature, filtered, and the cake is washed with water. Warning: This cake still has explosive properties; never submit this cake to heat, friction, or impact. The wet cake is then suspended in water (4.1 L). A sodium hydroxide aqueous solution is added in order to fully dissolve the reaction medium, followed by the addition of a 33% hydrochloric acid aqueous solution at 70 °C until pH is around 2. After cooling down to ambient temperature, the resulting suspension is filtered and the cake is washed with water. SIBX (605 g) is obtained after drying under vacuum. Warning: Any modification of the composition could give an explosive mixture. The homogeneity of the SIBX cake composition must be verified on milligram scale samples and must be guaranteed by a strict control of the process parameters.Handling, Storage, and Precautions: manipulation under a laminar flow extractor hood, storage in a well-sealed container protected from light and heat in a ventilated chemical storage cabinet. Use caution when using DMSO as solvent. Avoid adding SIBX to DMSO alone. Add SIBX powder onto the mixture containing the substance to be oxidized in DMSO.Instructions for Destruction: 2-iodoxybenzoic acid (1 equiv) oxidizes sodium metabisulfite (1 equiv) into sodium sulfate. For example, add 568 g (1 mol) of SIBX to a solution of sodium metabisulfite (209 g, 1.1 mol) in water (2 L). After stirring for 1 h, take a sample (about 10–50 mL) of the suspension and add 1 g of potassium iodide. If the supernatant solution is not brown (presence of iodine), add more sodium metabisulfite until IBX is totally reduced. Warning: A safety study must be performed before any synthesis or use of SIBX on kilogram scale or higher." @default.
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• W1904874611 date "2012-03-15" @default.
• W1904874611 modified "2023-09-25" @default.
• W1904874611 title "Stabilized 2-Iodoxybenzoic Acid (SIBX)" @default.
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• W1904874611 doi "https://doi.org/10.1002/047084289x.rn01376" @default.
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