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Isothiazole information


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
CAS Number
  • 288-16-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:35600 checkY
ChemSpider
  • 60838 checkY
ECHA InfoCard 100.241.294 Edit this at Wikidata
PubChem CID
  • 67515
UNII
  • 38FAO14250 checkY
CompTox Dashboard (EPA)
  • DTXSID90182980 Edit this at Wikidata
InChI
  • 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
SMILES
  • n1sccc1
Properties
Chemical formula
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 checkY☒N ?)
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.

  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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Isothiazole

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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. The isomeric...

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Isothiazolinone

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the formula (CH)2SN(H)CO. A white solid, it is structurally related to isothiazole. Isothiazolone itself is of limited interest, but several of its derivatives...

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Benzisothiazolinone

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the formula C6H4SN(H)CO. A white solid, it is structurally related to isothiazole, and is part of a class of molecules called isothiazolinones. BIT is...

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Azole

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4-Oxadiazole) Furazan (1,2,5-oxadiazole) 1,3,4-oxadiazole N,S compounds Thiazole Isothiazole Thiadiazole (1,2,3-Thiadiazole) 1,2,4-thiadiazole 1,2,5-thiadiazole 1...

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Heterocyclic compound

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which is nitrogen, are collectively called the azoles. Thiazoles and isothiazoles contain a sulfur and a nitrogen atom in the ring. Dithiolanes have two...

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Persistent carbene

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generated salt giving the impression of a H–X insertion. The reported stable isothiazole carbene (2b) derived from an isothiazolium perchlorate (1) was questioned...

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Lurasidone

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hydroxylation of the cyclohexane ring and reductive cleavage of the isothiazole ring followed by S-methylation. The two relevant active metabolites are...

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C3H3NS

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C3H3NS (molar mass: 85.13 g/mol, exact mass: 84.9986 u) may refer to: Isothiazole, or 1,2-thiazole Thiazole, or 1,3-thiazole This set index page lists...

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Oxathiazolones

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electron deficient dipolariphile to give stable heterocycles such as isothiazole (seen below). The intermediate has been successfully trapped using other...

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List of compounds with carbon number 3

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288-14-2 C3H3NO oxazole 288-42-6 C3H3NO propiolamide 7341-96-0 C3H3NS isothiazole 288-16-4 C3H3NS thiazole 288-47-1 C3H3O propenoyl radical 72241-20-4...

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Ochroconis lascauxensis

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involving benzalkonium chloride, miristalkonium chloride, and 2-octyl-2H-isothiazole-3-one, which resulted in a net decrease of fifty percent of the fungus...

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Organosulfur chemistry

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dithietanes, thiolanes, thianes, dithianes, thiepanes, thiepines, thiazoles, isothiazoles, and thiophenes, among others. The latter three compounds represent a...

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Electrophilic fluorination

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However, the specialized reagent 2-fluoro-3,3-dimethyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide consistently affords better yields of monofluorinated carbonyl...

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AKR1B1

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novel naphtho[1,2-d]isothiazole acetic acid derivative (3) 2nvd: Human Aldose Reductase complexed with novel naphtho[1,2-d]isothiazole acetic acid derivative...

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Thiomuscimol

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Thiomuscimol is a GABAA receptor agonist which is structurally related to muscimol. Lykkeberg, Jytte; Krogsgaard-Larsen, Povl; Garegg, Per J.; Norberg...

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Amflutizole is a xanthine oxidase inhibitor used for the treatment of gout. O'Regan MH, Smith-Barbour M, Perkins LM, Cao X, Phillis JW (October 1994)....

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Fananserin

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name 2-(3-(4-(p-Fluorophenyl)-1-piperazinyl)propyl)-2H-naphth(1,8-cd)isothiazole 1,1-dioxide CAS Number 127625-29-0 Y PubChem CID 60785 IUPHAR/BPS 5434...

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