Stabilized 2-Iodoxybenzoic Acid

Since 1994,1 2-iodoxybenzoic acid (IBX), has been well recognized as a very powerful and selective oxidizing agent. Like, Dess-Martin periodinane, IBX is an environmentally benign alternative to metal-based oxidizing agents. However, IBX is not often used, due to the fact it is and impact-sensitive explosive material, preventing its shipping and transport, as well as application in industry.2 In 2003, a stabilized formulation of IBX (SIBX) was reported3 which displayed none of the explosive properties of IBX, while maintaining excellent reactivity and selectivity. SIBX was then employed in a series of oxidations of aliphatic, allylic, and benzylic alcohols. The reactions proceeded cleanly, with yields comparable to those obtained with unstabilized IBX or Dess-Martin periodinane (Scheme 1). Additionally, SIBX is capable of oxidative demethylation of 2-methoxyphenols in good to excellent yields. In one demonstrated case, oxidation proceeds in excellent yield without the loss of the silyl protecting group (Scheme 2). Another report demonstrated the use of SIBX in the oxidative dearomatization of 2-alkylphenols into orthoquinols (Scheme 3).4 This route is a useful alternative to the Barton oxidation, which uses a selenium-based reagent, or the periodate-mediated Adler oxidation. Sigma-Aldrich is pleased to introduce SIBX for your research needs. Product Name Product #  2-Iodoxybenzoic acid, stabilized (45 wt.% IBX)   661384

References:

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.