5048. o-Iodoxybenzoic Acid

Nomenclature

CAS number: 64297-64-9; 61717-82-6 (cyclic tautomer)
2-Iodylbenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide; IBX; 2-iodoxybenzoic acid.
C7H5IO4; mol wt 280.02.
C 30.02%, H 1.80%, I 45.32%, O 22.85%.

Description and references

Hypervalent 10-I-4 iodine reagent; cyclic tautomer is the predominant molecular structure. Prepn: C. Hartmann, V. Meyer, Ber. 26, 1727 (1893); F. R. Greenbaum, Am. J. Pharm. 108, 17 (1936); and conversion to stable 12-I-5 periodinanes: D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 113, 7277 (1991). Improved prepn: M. Frigerio et al., J. Org. Chem. 64, 4537 (1999). Prepn of a stabilized, nonexplosive formulation: D. Depernet, B. Francois, US 6462227 (2002 to Simafex). IR analysis: R. Bell, K. J. Morgan, J. Chem. Soc. 1960, 1209. Crystal structure: J. Z. Gougoutas, Acta Crystallogr. 10, 489 (1981). 13C NMR analysis: A. R. Katritzky et al., Magn. Reson. Chem. 27, 1007 (1989). Oxidizing properties and reaction conditions: M. Frigerio et al., J. Org. Chem. 60, 7272 (1995). Kinetics and mechanism of oxidation reactions: S. De Munari et al., ibid. 61, 9272 (1996). Characterization of crystallographic forms: P. J. Stevenson et al., J. Chem. Soc. Perkin Trans. 2 1997, 589. Brief review of chemistry: T. Wirth, Angew. Chem. Int. Ed. 40, 2812-2814 (2001).

Chemical structure

Properties

White crystalline solid, mp 233° (dec). Virtually insol in common organic solvents; insol in water. Soly in DMSO: 1.5 M. Sol in aq pyridine, aq sodium hydroxide (dec).

Caution

Explosive under impact or heating >200°: J. B. Plumb, D. J. Harper, Chem. Eng. News 68, 3 (July 16, 1990).

Use

Mild, chemoselective, environmentally friendly oxidizing agent. In prepn of Dess-Martin periodinane, q.v.