Isothiazole

Isothiazole

Names
Preferred IUPAC name 1,2-Thiazole [1]
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) [2]
Acidity (pKa)	−0.5 (of conjugate acid) [3]
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.

See also

• Isothiazolinone

References

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. Isothiazoles, D. W. Brown and M. Sainsbury, page 513
3. Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978)
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.