515845-18-8

Basic information

• Product Name: 1H-Pyrazole, 5-(4-methylphenyl)-1-phenyl-3-(trifluoromethyl)-
• CAS NO: 515845-18-8
• Molecular Formula: C17H13F3N2
• Molecular Weight: 302.299
• Mol File: 515845-18-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole, 5-(4-methylphenyl)-1-phenyl-3-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole, 5-(4-methylphenyl)-1-phenyl-3-(trifluoromethyl)-(515845-18-8)
• EPA Substance Registry System: 1H-Pyrazole, 5-(4-methylphenyl)-1-phenyl-3-(trifluoromethyl)-(515845-18-8)

Safety Data

• Hazardous Substances Data: 515845-18-8(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 26974-15-2 5-(4-methylbenzene)-3-(trifluoromethyl)-1H-pyrazole 
• 588-64-7 (E)-1-benzylidene-2-phenylhydrazine 
• 187812-31-3 1,1,1-trifluoro-4-methoxy-4-(4-methylphenyl)-3-buten-2-one 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 766-97-2 4-n-methylphenylacetylene 
• 96107-01-6 (E)-1,1,1,-trifluoro-4-(p-tolyl)but-3-en-2-one 
• 104-87-0 4-methyl-benzaldehyde 
• 887144-94-7 Togni's reagent II 
• 122-00-9 para-methylacetophenone 
• 720-94-5 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione 

Downstream Products

• 630389-87-6 2-methyl-5-[1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzenesulfonyl chloride 

Relevant articles and documents

Mild and Regioselective Synthesis of 3-CF3-Pyrazoles by the AgOTf-Catalysed Reaction of CF3-Ynones with Hydrazines

Gold- and silver-catalysed reactions of trifluoromethylated ynones with aryl (alkyl) hydrazines were investigated. The use of (THD-Dipp)AuOTf and AgOTf resulted in quick heterocyclization reactions to selectively give 3-CF3-pyrazoles. AgOTf was found to be the catalyst of choice, and various 3-CF3-pyrazoles were formed in up to 99 % isolated yield with high regioselectivity. The reaction has a broad scope: 3-CF3-pyrazoles with alkyl and aryl substituents as well as different functional groups can be prepared by this approach. The known pyrazole drugs Celebrex and SC-560 were efficiently prepared to demonstrate the utility of the method. Mechanistic investigations revealed that the reaction involves the formation of a hemiaminal as a key intermediate.

An efficient route to 3-trifluoromethylpyrazole via cyclization/1,5-H shift and its applications in the synthesis of bioactive compounds

A methodology for regioselective synthesis of 3-trifluoromethylpyrazole from the reaction of trifluoromethyl alkenone and tosylhydrazone has been developed. The reaction was proposed to proceed through a tandem cyclization and 1,5-H shift reaction, which can be applied to the synthesis of bioactive compounds like Celecoxib, Mavacoxib, and SC-560.

New strategy for the regioselective synthesis of 1-phenyl-3- trifluoromethyl-1H-pyrazoles

A regioselective synthesis of 3-trifluoromethyl-1-phenyl-1H-pyrazoles (1,3-isomers) as well as their 1,5-isomers (5-trifluoromethyl-1-phenyl-1H- pyrazoles), is described. The 1,3-isomers were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with arylhydrazones followed by deprotective hydrolysis while the 1,5-isomer was obtained by direct cyclocondensation of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with phenylhydrazine. An unequivocal assignment of the 1,3- and 1,5-isomers of the pyrazole products is given.