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Isothiazole

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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)^[3]

Acidity (pK_a)

-0.5 (of conjugate acid)^[2]

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

[edit]

^ 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.

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Retrieved from "https://en.wikipedia.org/w/index.php?title=Isothiazole&oldid=1182520802" Categories: ●Isothiazoles ●Heterocyclic compound stubs Hidden categories: ●Articles without KEGG source ●ECHA InfoCard ID from Wikidata ●Articles containing unverified chemical infoboxes ●Chembox image size set ●Articles with short description ●Short description matches Wikidata ●All stub articles ●This page was last edited on 29 October 2023, at 21:07 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view