2-Mercaptopyridine N-oxide is used in ratiometric fluorescence imaging of intracellular zinc ions in mammalian cultures. It is used in the radical coupling of benzoyl derivatives of 2-deoxy-D-ribose, with heterocyclic bases to give C-nucleosides. It acts as a ligand and form coordination complexes with palladium chloride. It is a precursor to O-acyl thiohydroxamates. Further, it serves as an antifungal agent. In addition to this, it is used in the preparation of 1-oxa-2-oxo-3-thia-indolizinium chloride by reaction with carbonyl dichloride.
Thermal decomposition of O-acyl derivatives generates alkyl radicals: Tetrahedron Lett., 26, 5939, 5943 (1985). Reaction with Bu3SnH leads to decarboxylation: J. Chem. Soc., Chem. Commun., 939 (1983); Tetrahedron, 41, 3901 (1985):
This sequence has also been applied to the esters with amino acids, prepared by mixed anhydride coupling using isobutyl chloroformate: J. Chem. Soc., Chem. Commun., 1298 (1984). The active esters have also been applied to formatiion of amides and peptides: Tetrahedron, 52, 9347, 9367 (1996).
Decomposition of the ester in CCl4 gives the alkyl chloride: Tetrahedron Lett., 24, 4979 (1983), in BrCCl3 the alkyl bromide, and in CHI3, the iodide: Tetrahedron, 43, 4321 (1987); Org. Synth., 75, 124 (1997). Similarly, decarboxylation in the presence of Diphenyl diselenide, A13919 , results in phenylselenoethers, which can be used to introduce a double bond via selenoxide elimination: Heterocycles, 25, 449 (1987); J. Org. Chem., 55, 2282 (1990).
Has been used in the radical coupling of benzoyl derivatives of 2-Deoxy-D-ribose, A11990 , with heterocyclic bases to give C-nucleosides: Chem. Lett., 1673 (1992).
Bretti, C.; Cigala, R. M.; Crea, F.; De Stefano, C.; Lando, G.; Sammartano, S. Thermodynamics of Zn2+ 2-mercaptopyridine-N-oxide and 2-hydroxypyridine-N-oxide interactions: Stability, solubility, activity coefficients and medium effects. J. Mol. Liq. 2015, 211, 876-884.
Bretti, C.; Cigala, R. M.; Lando, G.; Milea, D.; Sammartano, S. Some Thermodynamic Properties of Aqueous 2-Mercaptopyridine-N-Oxide (Pyrithione) Solutions. J. Solution Chem. 2014, 43 (6), 1093-1109.
Zhang, G. Polymorphism in unusual one-dimensional coordination polymers based on cadmium(II) and 2-mercaptopyridine N-oxide. CrystEngComm 2013, 15 (33), 6453-6456.
Gefahrenhinweise (EU): H301-H315-H319-H335
Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.