1432595-88-4

Basic information

• Product Name: (Z)-3-(2,5-dimethylphenyl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione
• Synonyms: (Z)-3-(2,5-dimethylphenyl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione
• CAS NO: 1432595-88-4
• Molecular Weight: 274.408
• Mol File: 1432595-88-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-3-(2,5-dimethylphenyl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-(2,5-dimethylphenyl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione(1432595-88-4)
• EPA Substance Registry System: (Z)-3-(2,5-dimethylphenyl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione(1432595-88-4)

Safety Data

• Hazardous Substances Data: 1432595-88-4(Hazardous Substances Data)

Upstream product

• 2168-83-4 thiophene-2-carbodithioic acid methyl ester 
• 2142-73-6 1-(2,5-dimethylphenyl)-1-ethanone 

Downstream Products

• 1432595-99-7 5-(2,5-dimethylphenyl)-1-(4-methoxyphenyl)-3-(thien-2-yl)-1Hpyrazole 
• 1417890-59-5 (Z)-1-(2,5-dimethylphenyl)-3-(methylthio)-3-(thiophen-2-yl)-prop-2-en-1-one 
• 1432596-22-9 (E)-1-(2,5-dimethylphenyl)-3-(methylthio)-3-(thiophen-2-yl)-prop-2-en-1-one 

Relevant articles and documents

Cyclocondensation of arylhydrazines with 1,3-bis(het)arylmonothio-1,3- diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity

Two efficient highly regioselective routes for the synthesis of unsymmetrically substituted 1-aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity starting from active methylene ketones have been reported. In the first protocol, the newly synthesized 1,3-bis(het)aryl-monothio-1,3-diketone precursors (prepared by condensation of active methylene ketones with het(aryl) dithioesters in the presence of sodium hydride) were reacted with arylhydrazines in refluxing ethanol under neutral conditions, furnishing 1-aryl-3,5-bis(het)arylpyrazoles 7, in which the het(aryl) moiety attached to the thiocarbonyl group of monothio-1,3-diketones is installed at the 3-position. In the second method, the corresponding 3-(methylthio)-1,3-bis(het)aryl-2- propenones (prepared in situ by base-induced alkylation of 1,3- monothiodiketones) were condensed with arylhydrazines in the presence of potassium tert-butoxide in refluxing tert-butyl alcohol, yielding 1-aryl-3,5-bis(het)arylpyrazoles 9 with complementary regioselectivity (method A). The efficiency of this protocol was further improved by developing a one-pot, three-component procedure for the synthesis of pyrazoles 9, directly from active methylene ketones, by reacting in situ generated 3-(methylthio)-1,3-bis(het)aryl-2-propenones with arylhydrazines in the presence of sodium hydride (instead of potassium tert-butoxide as base). The structures and regiochemistry of newly synthesized pyrazoles were confirmed from their spectral and analytical data along with X-ray crystallographic data of three pairs of regioisomers.