| Identification | Back Directory | [Name]
Isothiazole | [CAS]
288-16-4 | [Synonyms]
EOS-61208
Isothiazole
1,2-Thiazol
1,2-thiazole
2-Azathiophene
Isothiazole> | [Molecular Formula]
C3H3NS | [MDL Number]
MFCD00020818 | [MOL File]
288-16-4.mol | [Molecular Weight]
85.13 |
| Chemical Properties | Back Directory | [Melting point ]
176 °C (decomp)(Solv: water (7732-18-5)) | [Boiling point ]
114°C(lit.) | [density ]
1.1566 (rough estimate) | [refractive index ]
1.5280 to 1.5320 | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Oil | [pka]
4.00±0.12(Predicted) | [color ]
Clear Colourless | [λmax]
242nm(lit.) |
| Hazard Information | Back Directory | [Chemical Properties]
Isothiazole is a colorless liquid with a pyridine-like odor. It is only slightly soluble in water but readily dissolves in organic solvents such as ethanol and benzene. When treated with butyl lithium at -70°C, it undergoes lithiation at the 5-position. Isothiazole serves as a versatile intermediate for the synthesis of various 5-substituted derivatives, including alkyl groups (R-), formyl (-CHO), carboxyl (-COOH), and acyl groups (RCO-), among others. Electrophilic substitution reactions, such as nitration, sulfonation, and halogenation, predominantly occur at the 4-position. | [Uses]
Isothiazole, is a versatile building block that can be used in the synthesis of more complex compounds with biological activity such as the pharmaceutical drugs ziprasidone (Z485000), and perospirone (P288900). | [Definition]
ChEBI: Isothiazole is a mancude organic heteromonocyclic parent, a monocyclic heteroarene and a member of 1,2-thiazoles. | [References]
[1] LAI CHEN. Discovery of Novel Isothiazole, 1,2,3-Thiadiazole, and Thiazole-Based Cinnamamides as Fungicidal Candidates[J]. Journal of Agricultural and Food Chemistry, 2019, 67 45: 12357-12365. DOI:10.1021/acs.jafc.9b03891.
[2] A. KLETSKOV. Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes[J]. Synthesis-Stuttgart, 2019, 113 1: 159-188. DOI:10.1055/s-0039-1690688.
[3] BERA A, PATRA P, AZAD A, et al. Neat synthesis of isothiazole compounds, and studies on their synthetic applications and photophysical properties?[J]. New Journal of Chemistry, 2022, 24: 11685-11694. DOI:10.1039/D2NJ01962K.
[4] ZHU-ZHU ZHANG. Synthesis of Isoselenazoles and Isothiazoles from Demethoxylative Cycloaddition of Alkynyl Oxime Ethers[J]. The Journal of Organic Chemistry, 2020, 86 1: 632-642. DOI:10.1021/acs.joc.0c02286. |
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