Isothiazole
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| Names | |||
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| Preferred IUPAC name 1,2-Thiazole[1] | |||
| Other names isothiazole | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.241.294 | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| 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). | |||
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
- ^ 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.