2-sulfanylpyridin-1-ium-1-olate

• ChemBase ID: 146070
• Molecular Formular: C5H5NOS
• Molecular Mass: 127.1643
• Monoisotopic Mass: 127.00918479
• SMILES: c1cc[n+](c(c1)S)[O-]
• Canonical SMILES: Sc1cccc[n+]1[O-]
• InChI: InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H
• InChIKey: FGVVTMRZYROCTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-sulfanylpyridin-1-ium-1-olate
• IUPAC Traditional name: 2-mercaptopyridine n-oxide
• Synonyms: 2-Mercaptopyridine-1-oxide; 2-Mercaptopyridine N-oxide; 2-Pyridinethiol-1-oxide; Pyrithione; 1-Hydroxypyridine-2-thione; 2-Pyridinethiol N-oxide; 2-巯基吡啶-1-氧化物; 2-巯基吡啶-N-氧化物; 2-硫代-1-氧化吡啶; 吡啶硫酮; 2-巯基吡啶 N-氧化物

Database IDs

• CAS Number: 1121-31-9
• EC Number: 214-329-4
• MDL Number: MFCD00006196
• Beilstein Number: 109936; 906983
• Merck Index: 147994
• PubChem SID: 24851166; 162240269
• PubChem CID: 1570

CALCULATED PROPERTIES

• LogD (pH = 5.5): 0.17694847
• LogD (pH = 7.4): -0.4128268
• Log P: 0.19550161
• Molar Refractivity: 34.4765 cm^3
• Polarizability: 12.957596 Å^3
• Polar Surface Area: 26.94 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 6.8428946
• H Acceptors: 1
• H Donor: 1

PROPERTIES

Physical Property

• Melting Point: 69-72 °C(lit.); 69-72°C; 70-72 °C

Safety Information

• Storage Warning: Air & Light Sensitive
• RTECS: UT8999000
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥97.0% (T); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C5H5NOS

DETAILS

Sigma Aldrich - 188549

Application
Precursor to O-acyl thiohydroxamates.1 Ligates to metals to form biologically active complexes.2,3,4
Packaging
5, 25 g in glass bottle

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).