Pyrithione
Chemical compound / From Wikipedia, the free encyclopedia
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Pyrithione is the common name of an organosulfur compound with molecular formula C
5H
5NOS, chosen as an abbreviation of pyridinethione, and found in the Persian shallot.[4] It exists as a pair of tautomers, the major form being the thione 1-hydroxy-2(1H)-pyridinethione and the minor form being the thiol 2-mercaptopyridine N-oxide; it crystallises in the thione form.[5] It is usually prepared from either 2-bromopyridine,[1] 2-chloropyridine,[6][7] or 2-chloropyridine N-oxide,[8] and is commercially available as both the neutral compound and its sodium salt.[1] It is used to prepare zinc pyrithione,[9][10] which is used primarily to treat dandruff and seborrhoeic dermatitis in medicated shampoos,[11][12] though is also an anti-fouling agent in paints.[13]
Interconversion of pyrithione tautomers thione form on the left, thiol form on the right | |
Names | |
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Preferred IUPAC name
1-Hydroxy-2(1H)-pyridinethione (thione) 2-Pyridinethiol 1-oxide (thiol) | |
Other names
Omadine thione: 1-Hydroxypyridine-2-thione N-Hydroxypyridine-2-thione thiol: 2-Mercaptopyridine monoxide 2-Mercaptopyridine N-oxide 2-Mercaptopyridine 1-oxide | |
Identifiers | |
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3D model (JSmol) |
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109936 | |
ChEBI |
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ChEMBL |
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ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.013.027 |
EC Number |
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913415 | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C5H5NOS | |
Molar mass | 127.16 g·mol−1 |
Appearance | Beige crystalline powder |
Melting point | 70 to 73 °C (158 to 163 °F; 343 to 346 K) |
2.5 g L−1 at 20 °C | |
Solubility | Soluble: benzene, chloroform, dichloromethane, dimethylformamide, dimethylsulfoxide, ethyl acetate[1] Slightly soluble: diethyl ether, ethanol, methyl tert-butyl ether, tetrahydrofuran[1] |
Acidity (pKa) | −1.95 (proton addition), 4.6[2][3] |
Hazards | |
GHS labelling: | |
Danger | |
H301, H315, H319, H335 | |
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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