sodium (1-oxidopyridin-1-ium-2-yl)sulfanide

• ChemBase ID: 85630
• Molecular Formular: C5H4NNaOS
• Molecular Mass: 149.14613
• Monoisotopic Mass: 148.99112903
• SMILES: [n+]1(ccccc1[S-])[O-].[Na+]
• Canonical SMILES: [S-]c1cccc[n+]1[O-].[Na+]
• InChI: InChI=1S/C5H5NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4,8H;/q;+1/p-1
• InChIKey: WNGMMIYXPIAYOB-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (1-oxidopyridin-1-ium-2-yl)sulfanide
• IUPAC Traditional name: sodium (1-oxidopyridin-1-ium-2-yl)sulfanide
• Synonyms: 2-Mercaptopyridine-1-oxide sodium salt; 2-Mercaptopyridine N-oxide, sodium salt; Sodium pyridine-2-thiolate N-oxide; 2-Mercaptopyridine-N-oxide, sodium salt; Sodium omadine; Sodium pyridine-2-thiolate N-oxide, 40% aqueous solution; Pyrithione sodium salt; 2-Mercaptopyridine N-oxide sodium salt; 1-Hydroxy-2-pyridinethione sodium salt; 2-Pyridinethiol-1-oxide sodium salt; 2-Mercaptopyridine N-oxide sodium salt solution; 2-Mercaptopyridine N-oxide sodium salt, anhydrous; 2-巯基吡啶 N-氧化物 钠盐; 1-羟基-2-吡啶硫酮 钠盐; 2-巯基吡啶-1-氧化物 钠盐; 2-硫代-1-氧化吡啶 钠盐; 2-巯基吡啶-N-氧化物 钠盐; 吡啶硫酮 钠盐; 2-巯基吡啶-N-氧化物 钠盐 溶液; 2-巯基吡啶 N-氧化物 钠盐 无水

Database IDs

• CAS Number: 3811-73-2
• EC Number: 223-296-5
• MDL Number: MFCD01941547
• Beilstein Number: 4026050
• Merck Index: 147994
• PubChem SID: 24882941; 24859767; 24895565; 162072746
• PubChem CID: 19658

CALCULATED PROPERTIES

• Acid pKa: 6.8428946
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.17694847
• LogD (pH = 7.4): -0.4128268
• Log P: 0.19550161
• Molar Refractivity: 31.6388 cm^3
• Polarizability: 13.255843 Å^3
• Polar Surface Area: 26.94 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 M at 20 °C, clear, faintly yellow
• Apperance: very deep brown
• Melting Point: -30 to -25°C; 69-72°C; ca 290°C dec.
• Boiling Point: 109°C; ca 290(dec.)°C
• Density: 1.238

Safety Information

• Storage Warning: Harmful/Irritant/Hygroscopic/Stench; Hygroscopic
• RTECS: UT9000000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26; 26-36; 26-36/37; 26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥96%; ≥96.0% (NT); 40% aq. soln.; 95%; 98%
• Concentration: ~40% in H2O
• Impurities: <0.001% Phosphorus (P); <0.1% Insoluble matter
• Cation Traces: Al: <0.0005%; Ca: <0.005%; Cu: <0.0005%; Fe: <0.0005%; K: <0.01%; Mg: <0.001%; Pb: <0.001%; Zn: <0.0005%
• Empirical Formula (Hill Notation): C5H4NNaOS

DETAILS

Sigma Aldrich - H3261

Biochem/physiol Actions
2-Mercaptopyridine N-oxide is a zinc ionophore that transports zinc into cells1.
Application
2-Mercaptopyridine N-oxide can be used to generate bidentate oxothiolane chelates with transition metals.
2-Mercaptopyridine N-oxide, also called pyrithione, is added to cells in culture so metals enter them readily without relying on transporters. 2-Mercaptopyridine N-oxide can be used to generate bidentate oxothiolane chelates with transition metals. It is used to study picornavirus infections1 and is used as a zinc ionophore.

Sigma Aldrich - 329061

Application
For chemistry of 2-mercaptopyridine-N-oxide, see Aldrichimica Acta.1
Packaging
5 g in glass bottle

Sigma Aldrich - 63846

Packaging
500 mL in glass bottle

Sigma Aldrich - 63844

Other Notes
Esters of carboxylic acids with this N-oxide undergo decarboxylative free radical chain reactions1,2,3,4