Stabilized 2-Iodoxybenzoic Acid (SIBX)

ChemFiles 2006, 6.2, 14.

Since 1994,1 2-iodoxybenzoic acid (IBX) has been well recognized as a very powerful and selective oxidizing agent. Similar to the Dess–Martin periodinane, IBX is an environmentally benign alternative to metal-based oxidizing agents. However, IBX is not often used due to the fact that it is an impact-sensitive explosive material, which prevents its shipping and transport, as well as its application in industry.2 We are pleased to introduce a stabilized formulation of IBX (SIBX) that displays none of the explosive properties of IBX, while maintaining excellent reactivity and selectivity.

SIBX has demonstrated use in the:

  • Oxidation of alcohols to carbonyl compounds.3
  • Oxidative demethylation of 2-methoxyphenols.3
  • Oxidative dearomatization of 2-alkylphenols into orthoquinols (alternative to Barton or Adler oxidations).4

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  1. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
  2. Plumb, J. B.; Harper, D. J. Chem. Eng. News 1990, 68, 3.
  3. Ozanne, A. et al. Org. Lett. 2003, 5, 2903.
  4. Quideau, S. et al. Arkivoc, 2003, 6, 106.

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