Isothiazole

Isothiazole
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Names
	Preferred IUPAC name 1,2-Thiazole
	Other names isothiazole
Identifiers
CAS Number	288-16-4 Y;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35600 Y;
ChemSpider	60838 Y;
ECHA InfoCard	100.241.294
PubChem CID	67515;
UNII	38FAO14250 Y;
CompTox Dashboard (EPA)	DTXSID90182980 ;
	InChI InChI=1S/C3H3NS/c1-2-4-5-3-1/h1-3H Y Key: ZLTPDFXIESTBQG-UHFFFAOYSA-N Y; InChI=1/C3H3NS/c1-2-4-5-3-1/h1-3H Key: ZLTPDFXIESTBQG-UHFFFAOYAS;
	SMILES n1sccc1;
Properties
Chemical formula	C3H3NS
Molar mass	85.12 g·mol−1
Boiling point	114 °C (237 °F; 387 K)
Acidity (pKa)	−0.5 (of conjugate acid)
Related compounds
Related compounds	thiazole, isoxazole
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Isothiazole, or 1,2-thiazole, is an organic compound consisting with the formula (CH)₃S(N). The ring is unsaturated and features an S-N bond.⁴ The isomeric thiazole, where the S and N are not directly bonded are far more common.

Isothiazones are produced by oxidation of enamine-thiones.⁵ The ring structure of isothiazole is incorporated into larger compounds with biological activity such as the pharmaceutical drugs ziprasidone and perospirone.

References

International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 140. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978)
Isothiazoles, D. W. Brown and M. Sainsbury, page 513
Heterocyclic Chemistry, 3rd Edition, J.A. Joule, K. Mills, and G.F. Smith, page 394
Kaur, Navjeet (2023). "Five-membered S,N-heterocycles". 5-Membered Heterocycle Synthesis Using Iodine. pp. 435–472. doi:10.1016/B978-0-443-18941-8.00007-9. ISBN 9780443189418.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 140. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[2] Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978)

[3] Isothiazoles, D. W. Brown and M. Sainsbury, page 513

[4] Heterocyclic Chemistry, 3rd Edition, J.A. Joule, K. Mills, and G.F. Smith, page 394

[5] Kaur, Navjeet (2023). "Five-membered S,N-heterocycles". 5-Membered Heterocycle Synthesis Using Iodine. pp. 435–472. doi:10.1016/B978-0-443-18941-8.00007-9. ISBN 9780443189418.

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See also

References