Pyrithione

Pyrithione
	; Interconversion of pyrithione tautomers; thione form on the left, thiol form on the right
Names
	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
CAS Number	thione: 1121-30-8; thiol: 1121-31-9; 3811-73-2 thiolate salt: sodium 2-pyridinethiolate 1-oxide; 15922-78-8 thione salt: sodium 2-thioxo-1(2H)-pyridinolate;
3D model (JSmol)	thione: Interactive image; thiol: Interactive image; thiolate salt: Interactive image; thione salt: Interactive image;
Beilstein Reference	109936
ChEBI	thione: CHEBI:36578; thiol: CHEBI:36584;
ChEMBL	thione: ChEMBL1650619; thiol: ChEMBL1356238;
ChemSpider	thione: 1514; thiol: 10446934; 1513 thiolate salt; 18517 thione salt;
DrugBank	DB06815;
ECHA InfoCard	100.013.027
EC Number	214-328-9; thione: 214-329-4;
Gmelin Reference	913415
PubChem CID	thione: 1570; 23685289 sodium pyrithione salt;
UNII	6GK82EC25D ;
CompTox Dashboard (EPA)	DTXSID00149908 ;
	InChI thione: InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,7H Key: YBBJKCMMCRQZMA-UHFFFAOYSA-N; thiol: InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H Key: FGVVTMRZYROCTH-UHFFFAOYSA-N; thiolate salt: InChI=1S/C5H5NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4,8H;/q;+1/p-1 Key: WNGMMIYXPIAYOB-UHFFFAOYSA-M; thione salt: InChI=1S/C5H4NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4H;/q-1;+1 Key: XNRNJIIJLOFJEK-UHFFFAOYSA-N;
	SMILES thione: c1ccn(c(=S)c1)O; thiol: C1=CC=[N+](C(=C1)S)[O-]; thiolate salt: c1cc[n+](c(c1)[S-])[O-].[Na+]; thione salt: c1ccn(c(=S)c1)[O-].[Na+];
Properties
Chemical formula	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)
Solubility in water	2.5 g L−1 at 20 °C
Solubility	Soluble: benzene, chloroform, dichloromethane, dimethylformamide, dimethylsulfoxide, ethyl acetate; Slightly soluble: diethyl ether, ethanol, methyl tert-butyl ether, tetrahydrofuran
Acidity (pKa)	−1.95 (proton addition), 4.6
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	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). Infobox references

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. 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. It is usually prepared from either 2-bromopyridine, 2-chloropyridine, or 2-chloropyridine N-oxide, and is commercially available as both the neutral compound and its sodium salt. It is used to prepare zinc pyrithione, which is used primarily to treat dandruff and seborrhoeic dermatitis in medicated shampoos, though is also an anti-fouling agent in paints.

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