Isothiazole

Isothiazole
Full structural formula
Skeletal formula with numbers
Ball-and-stick model
Space-filling model
Names
Preferred IUPAC name
1,2-Thiazole[1]
Other names
isothiazole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.241.294 Edit this at Wikidata
UNII
  • InChI=1S/C3H3NS/c1-2-4-5-3-1/h1-3H checkY
    Key: ZLTPDFXIESTBQG-UHFFFAOYSA-N checkY
  • InChI=1/C3H3NS/c1-2-4-5-3-1/h1-3H
    Key: ZLTPDFXIESTBQG-UHFFFAOYAS
  • n1sccc1
Properties
C3H3NS
Molar mass 85.12 g·mol−1
Boiling point 114 °C (237 °F; 387 K)[3]
Acidity (pKa) −0.5 (of conjugate acid)[2]
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).
checkY verify (what is checkYX markN ?)

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

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. ^ 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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