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1121-31-9 - 2-Mercaptopyridine N-oxide, 99% - 1-Hydroxypyridine-2-thione - 2-Pyridinethiol N-oxide - A14152 - Alfa Aesar

A14152 2-Mercaptopyridine N-oxide, 99%

Numéro CAS
1121-31-9
Synonymes
1-Hydroxypyridine-2-thione
2-Pyridinethiol N-oxide

Dimensions Prix ($) Quantité Disponibilité
5g 64,80
25g 155,00
100g 556,00
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2-Mercaptopyridine N-oxide, 99%

MDL
MFCD00006196
EINECS
214-329-4

Propriétés chimiques

Formule
C5H5NOS
Poids formulaire
127.17
Point de fusion
69-72°
Sensibilité
Air & Light Sensitive
Solubilité
Soluble in tris-hydrochloric acid.

Applications

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.

Notes

Incompatible with strong oxidizing agents and strong bases.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H301-H315-H319-H335

Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P261-P280-P301+P310-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,7994
Beilstein
906983
Code tarifaire harmonisé
2933.39
TSCA
Yes
RTECS
UT8999000

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