2-Mercaptopyridine N-oxide

• Catalog No.: A14152
• CAS Number: 1121-31-9
• M. F.: C5H5NOS
• M. W.: 127.1643
• Purity: 99%

SYNONYMS

• Title: 2-巯基吡啶 N-氧化物
• IUPAC name: 2-sulfanylpyridin-1-ium-1-olate
• IUPAC Traditional name: 2-mercaptopyridine n-oxide
• Synonyms: 1-Hydroxypyridine-2-thione; 2-Pyridinethiol N-oxide

DATABASE IDS

• Merck Index: 147994
• CAS Number: 1121-31-9
• Beilstein Number: 906983
• MDL Number: MFCD00006196
• EC Number: 214-329-4

PROPERTIES

• Safety Statements: 26-36/37
• Storage Warning: Air & Light Sensitive
• TSCA Listed: 是
• GHS Hazard statements: H301-H315-H319-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Risk Statements: 22-36/37/38
• RTECS: UT8999000
• Purity: 99%
• Melting Point: 69-72°C

REFERENCES

• 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).