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
• Article Data: 6

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

General Description

3-Phenylisothiazol-5-amine is a chemical compound featuring the chemical class of organoheterocyclic compounds known as benzisothiazoles. These are aromatic compounds encompassing a benzene ring fused to an isothiazole ring. 3-Phenylisothiazol-5-amine can be recognized by its molecular formula C9H8N2S and its systematic name is 3-phenyl-1,2-thiazol-5-amine. The molecular weight of the compound is 176.24 g/mol. This chemical falls under the category of benzisothiazole derivatives which are used in various pharmaceutical and chemical industries. It is generally used as a reactive compound in the creation of more complex chemical structures. The specific properties of this compound, including toxicity and environmental impact, will depend on the exact details of use and disposal.

Upstream product

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

Downstream Products

• 75907-56-1 2-[(3-Phenyl-isothiazol-5-ylamino)-methylene]-malonic acid diethyl ester 
• 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 
• 16188-24-2 3-(2,4-dichloro-phenyl)-5-methyl-isothiazole-4-carboxylic acid 
• 16188-23-1 3-(2,4-dichloro-phenyl)-5-methyl-isothiazole-4-carbonitrile 
• 16188-02-6 3-(4-chloro-phenyl)-5-methyl-isothiazole-4-carboxylic acid 
• 16188-01-5 3-(4-chloro-phenyl)-5-methyl-isothiazole-4-carbonitrile 

Relevant articles and documents

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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.