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188549 Aldrich

2-Mercaptopyridine N-oxide

99%

Synonym: 2-Pyridinethiol-1-oxide, Pyrithione

  • CAS Number 1121-31-9

  • Empirical Formula (Hill Notation) C5H5NOS

  • Molecular Weight 127.16

  •  Beilstein Registry Number 109936

  •  EC Number 214-329-4

  •  MDL number MFCD00006196

  •  PubChem Substance ID 24851166

  • Popular Documents:  FTIR (PDF)  

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Properties

Related Categories Building Blocks, C5, Chemical Synthesis, Heterocyclic Building Blocks, Pyridines More...
assay   99%
mp   69-72 °C(lit.)

Description

Packaging

5, 25 g in glass bottle

Application

2-Mercaptopyridine N-oxide was used to investigate the mechanism of photodegradation of mercaptopyridine-N-oxide biocides1. It was used in ratiometric fluorescence imaging of intracellular zinc ions in mammalian cultures2.

General description

2-Mercaptopyridine N-oxide forms complexes on reaction with palladium chloride3. It inhibits NADH-fumarate reductase purified from Trypanosoma cruzi4. It is precursor to O-acyl thiohydroxamates5. It ligates to metals to form biologically active complexes6,7,8.

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 3335
WGK Germany 
3
RTECS 
UT8999000

Protocols & Articles

Peer-Reviewed Papers

References

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1. Photodegradation of mercaptopyridine-N-oxide biocides. Neihof RA, Bailey CA, Patouillet C, et al. Arch. Environ. Contam. Toxicol. 8(3), 355-68, (1979)

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2. A tautomeric zinc sensor for ratiometric fluorescence imaging: application to nitric oxide-induced release of intracellular zinc. Chang CJ, Jaworski J, Nolan EM, et al. Proc. Natl. Acad. Sci. U. S. A. 101(5), 1129-34, (2004)

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3. Palladium complexes with simultaneous O: S coordination, syntheses, structures and characterization of complexes with 2-mercaptophenol or 2-mercaptopyridine N-oxide. Shi J-C, et al. Polyhedron 16(3), 369-75, (1997)

4. Mercaptopyridine-N-oxide, an NADH-fumarate reductase inhibitor, blocks Trypanosoma cruzi growth in culture and in infected myoblasts. Turrens JF, Newton CL, Zhong L, et al. FEMS Microbiol. Lett. 175(2), 217-21, (1999)

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5. J. Chem. Res. Synop., 30, (1990)

6. Aldrichimica Acta 20, 35, (1987)

7. ELEMENTAL SELENIUM GENERATED BY THE PHOTOBLEACHING OF SELENOMEROCYANINE PHOTOSENSITIZERS FORMS CONJUGATES WITH SERUM MACROMOLECULES THAT ARE TOXIC TO TUMOR CELLS. A.E. Underhill et al Phosphorus. Sulfur. Silicon Relat. Elem. 67, 311, (1992)

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8. J. Biopharm. Sci. 1, 331, (1990)

Beil. 21,V,7,150

Fieser 12,417 / Fieser 14,268 / Fieser 17,292

Aldrich MSDS 1, 1164:D / Corp MSDS 1 (2), 2213:B / FT-IR 2 (3), 3994:C / FT-IR 1 (2), 914:C / IR-Spectra (3), 1421:E / NMR-Reference 2 (2), 776:C / RegBook 1 (2), 2679:L / Structure Index 1, 421:A:5

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