14208-52-7

Basic information

• Product Name: 3-Phenylisothiazol-5-amine
• Synonyms: 3-Phenylisothiazol-5-amine;3-phenyl-1,2-thiazol-5-aMine
• CAS NO: 14208-52-7
• Molecular Formula: C₉H₈N₂S
• Molecular Weight: 176.23822
• Mol File: 14208-52-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-Phenylisothiazol-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenylisothiazol-5-amine(14208-52-7)
• EPA Substance Registry System: 3-Phenylisothiazol-5-amine(14208-52-7)

Safety Data

• Hazardous Substances Data: 14208-52-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenylisothiazol-5-amine is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of complex molecules with potential therapeutic applications, making it a valuable intermediate in drug development.
Used in Chemical Industry:
3-Phenylisothiazol-5-amine is used as a reactive compound in the synthesis of a wide range of chemical products. Its versatility in forming different chemical structures makes it an essential component in the production of various specialty chemicals and materials.
Used in Research and Development:
3-Phenylisothiazol-5-amine is used as a research compound for studying the properties and potential applications of benzisothiazole derivatives. Its role in the development of new chemical entities and understanding their interactions with biological systems is crucial for advancing scientific knowledge in this field.

Upstream product

• 16187-91-0 3-phenyl-3-iminothiopropionamide 
• 17196-74-6 (Z)-3-amino-3-phenylacrylonitrile 
• 614-16-4 Benzoylacetonitrile 
• 1823-99-0 3-amino-3-phenylacrylonitrile 

Downstream Products

• 90842-13-0 N-(3-phenyl-isothiazol-5-yl)-formamide 
• 13363-44-5 5-bromo-3-phenyl-isothiazole 
• 16187-93-2 4-bromo-3-phenyl-isothiazol-5-ylamine 
• 10514-34-8 3-phenylisothiazole 
• 21905-46-4 5-chloro-3-phenyl-isothiazole 
• 1239257-89-6 4-bromo-5-chloro-3-phenylisothiazole 
• 1438424-18-0 (R)-2-(5-cyano-6-(3-phenylisothiazol-5-ylamino)pyrazin-2-ylamino)butanamide 
• 1239252-79-9 N'-{4-[(4-bromo-3-phenylisothiazol-5-yl)oxy]-5-chloro-2-methylphenyl}-N-ethyl-N-methylimidoformamide 
• 1239252-66-4 N'-{4-[(4-chloro-3-phenylisothiazol-5-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide 
• 1239252-55-1 N'-{2,5-dimethyl-4-[(3-phenylisothiazol-5-yl)oxy]phenyl}-N-ethyl-N-methylimidoformamide 
• 1239257-88-5 4-[(4-bromo-3-phenylisothiazol-5-yl)oxy]-5-chloro-2-methylaniline 
• 1239257-87-4 4-chloro-3-phenylisothiazol-5-amine 
• 1239257-86-3 4,5-dichloro-3-phenylisothiazole 
• 1239257-85-2 4-[(4-chloro-3-phenylisothiazol-5-yl)oxy]-2,5-dimethylaniline 

Relevant articles and documents

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Pyrimidine benzamide-based thrombopoietin receptor agonists

A series of pyrimidine benzamide-based thrombopoietin receptor agonists is described. The lead molecule contains a 2-amino-5-unsubstituted thiazole, a group that has been associated with idiosyncratic toxicity. The potential for metabolic oxidation at C-5 of the thiazole, the likely source of toxic metabolites, was removed by substitution at C-5 or by replacing the thiazole with a thiadiazole. Potency in the series was improved by modifying the substituents on the pyrimidine and/or on the thiazole or thiadiazole pendant aryl ring. In vivo examination revealed that compounds from the series are not highly bioavailable. This is attributed to low solubility and poor permeability.

Phototransposition chemistry of phenylisothiazoles and phenylthiazoles. 1. Interconversions in benzene solution

Phenylthiazoles 1-3 and phenylisothiazoles 4-6 undergo phototransposition in benzene solvent mainly by P5, P6, and P7 permutation pathways. Phenylisothiazoles 5 and 6 also transpose via a P4 permutation process to yield phenylthiazoles 2 and 3 in less than 1% yield. In benzene saturated with D2O, 2-phenylthiazole (1) and 5-phenylisothiazole (6) each phototranspose to yield 4-deuterio-3-phenylisothiazole (4-D-4) and 4-phenylthiazole (2) without deuterium incorporation. Irradiation of 4-phenylthiazole (2) under these conditions results in rapid photodeuteration to yield 2-deuterio-4-phenylthiazole (2-D-2), which subsequently phototransposes to 5-deuterio-3-phenylisothiazole (5-D-3). These experimental results can be rationalized by a mechanism involving initial electrocyclic ring closure and sigmatropic shift of sulfur around the four sides of the azetine ring. Rearomatization of each bicyclic intermediate thus allows sulfur to insert into each position in the carbon-nitrogen sequence. As a consequence, these compounds divide into a tetrad in which isomers 1, 2,4, and 6 interconvert mainly via P5, P6, and P7 pathways and a dyad of two compounds in which 3 phototransposes to 5 via P5 and P7 pathways. Within the tetrad, BC-6, the bicyclic intermediate derived from 5-phenylisothiazoles (6), is postulated to undergo deuteration with simultaneous sigmatropic shift of sulfur when the reaction is carried out in benzene-D2O. This mechanistic view provides one coherent interpretation for the observed phototransposition and photodeuteration reactions.

RING-TRANSFORMATION FROM ISOTHIAZOLE TO 1,2,4-THIADIAZOLE - POSSIBLE INTERMEDIACY OF ?-SULFURANE

5-Amino-3-methyl- and 5-amino-3-phenylisothiazoles (3a and 3b) afforded 1:1 adducts with aromatic nitriles and imidates.On the basis of their spectral data and the structure of hydrolysis products, the adducts were identified as 3-substituted 5-(2-aminovinyl)-1,2,4-thiadiazole derivatives (2a-g), where ring transformation took place from isothiazole to 1,2,4-thiadiazole.