Isothiazole

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|Watchedfields = changed

|verifiedrevid = 443888553

|ImageFileL1 = Isothiazole 2D full aromatic.svg

|ImageSizeL1 = 120

|ImageAltL1 = Full structural formula

|ImageFileR1 = Isothiazole 2D numbered.svg

|ImageSizeR1 = 110

|ImageAltR1 = Skeletal formula with numbers

|ImageFileL2 = Isothiazole-3D-balls.png

|ImageSizeL2 = 120

|ImageAltL2 = Ball-and-stick model

|ImageFileR2 = Isothiazole-3D-spacefill.png

|ImageSizeR2 = 110

|ImageAltR2 = Space-filling model

|PIN = 1,2-Thiazole{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=140 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}

|OtherNames = isothiazole

|Section1={{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 60838

|InChI = 1/C3H3NS/c1-2-4-5-3-1/h1-3H

|InChIKey = ZLTPDFXIESTBQG-UHFFFAOYAS

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C3H3NS/c1-2-4-5-3-1/h1-3H

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = ZLTPDFXIESTBQG-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|??}}

|CASNo=288-16-4

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 38FAO14250

|PubChem = 67515

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 35600

|SMILES = n1sccc1

}}

|Section2={{Chembox Properties

| C=3 | H=3 | N=1 | S=1

|BoilingPtC=114

|BoilingPt_ref = [http://www.thieme-chemistry.com/fileadmin/Thieme/HW-100/pdf/june/0507_0572_Ksu_watermark.pdf Isothiazoles], D. W. Brown and M. Sainsbury, page 513

| pKa = −0.5 (of conjugate acid)Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978)

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|Section8={{Chembox Related

| OtherCompounds = thiazole, isoxazole

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Isothiazole, or 1,2-thiazole, is an organic compound consisting with the formula {{chem2|(CH)3S(N)}}. The ring is unsaturated and features an S-N bond.Heterocyclic Chemistry, 3rd Edition, J.A. Joule, K. Mills, and G.F. Smith, page 394 The isomeric thiazole, where the S and N are not directly bonded are far more common.

Isothiazones are produced by oxidation of enamine-thiones.{{cite book |doi=10.1016/B978-0-443-18941-8.00007-9 |chapter=Five-membered S,N-heterocycles |title=5-Membered Heterocycle Synthesis Using Iodine |date=2023 |last1=Kaur |first1=Navjeet |pages=435–472 |isbn=9780443189418 }}

The ring structure of isothiazole is incorporated into larger compounds with biological activity such as the pharmaceutical drugs ziprasidone and perospirone.