86201-92-5

Basic information

• Product Name: 1H-Pyrazole, 1-(4-chlorophenyl)-5-(2-furanyl)-3-(2-thienyl)-
• CAS NO: 86201-92-5
• Molecular Formula: C17H11ClN2OS
• Molecular Weight: 326.806
• Mol File: 86201-92-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole, 1-(4-chlorophenyl)-5-(2-furanyl)-3-(2-thienyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole, 1-(4-chlorophenyl)-5-(2-furanyl)-3-(2-thienyl)-(86201-92-5)
• EPA Substance Registry System: 1H-Pyrazole, 1-(4-chlorophenyl)-5-(2-furanyl)-3-(2-thienyl)-(86201-92-5)

Safety Data

• Hazardous Substances Data: 86201-92-5(Hazardous Substances Data)

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 1432595-93-1 (Z)-3-(furan-2-yl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione 
• 1073-69-4 N-4-chlorophenylhydrazine 

Downstream Products

• 138841-11-9 1-(4-Chloro-phenyl)-5-(5,6,7,8-tetrachloro-3a,9a-dihydro-benzo[b]furo[2,3-e][1,4]dioxin-2-yl)-3-thiophen-2-yl-1H-pyrazole 

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.