723-74-0

Basic information

• Product Name: 1-methyl-2-phenyl-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-one
• Synonyms: 1-methyl-2-phenyl-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-one
• CAS NO: 723-74-0
• Molecular Weight: 242.2
• Mol File: 723-74-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-methyl-2-phenyl-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2-phenyl-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-one(723-74-0)
• EPA Substance Registry System: 1-methyl-2-phenyl-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-one(723-74-0)

Safety Data

• Hazardous Substances Data: 723-74-0(Hazardous Substances Data)

Upstream product

• 59-88-1 phenylhydrazine hydrochloride 
• 96145-98-1 1-phenyl-3-trifluoromethyl-5-hydroxypyrazole 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 622-36-6 1-methyl-2-phenylhydrazine 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 781-93-1 3-trifluoromethyl-1-phenyl-1H-pyrazol-5(4H)-one 

Relevant articles and documents

Synthesis and biological evaluation of polyfluoroalkylated antipyrines and their isomeric O-methylpyrazoles

Background: Formally belonging to the non-steroidal anti-inflammatory drug class pyrazolones have long been used in medical practices. Objective: Our goal is to synthesize N-methylated 1-aryl-3-polyfluoroalkylpyrazolones as fluorinated analogs of antipyrine, their isomeric O-methylated derivatives resembling celecoxib structure and evaluate biological activities of obtained compounds. Methods: In vitro (permeability) and in vivo (anti-inflammatory and analgesic activities, acute toxicity, hyperalgesia, antipyretic activity, “open field” test) experiments. To suggest the mechanism of biological activity, molecular docking of the synthesized compounds was carried out into the tyrosine site of COX-1/2. Results: We developed the convenient methods for regioselective methylation of 1-aryl-3- polyfluoroalkylpyrazol-5-ols leading to the synthesis N-methylpyrazolones and O-methylpyrazoles as antipyrine and celecoxib analogs respectively. For the first time, the biological properties of new derivatives were investigated in vitro and in vivo. Conclusion: The trifluoromethyl antipyrine represents a valuable starting point in design of the lead series for discovery new antipyretic analgesics with anti-inflammatory properties.

Regiocontrolled N-, O- and C-methylation of 1-phenyl-3-polyfluoroalkyl-1H-pyrazol-5-ols

The approaches for regiocontrolled N-, O- and C-methylation of 1-phenyl-3-polyfluoroalkyl-1H-pyrazol-5-ols have been developed. The chemoselective N-methylation proved to be an efficient method for the synthesis of polyfluorinated antipyrine analogs. In addition, we reinvestigated the structure of 3-polyfluoroalkyl-1-phenylpyrazol-5-ols by the X-Ray analysis. The quantum-chemical calculations were used for an explanation of methylation processes. The preliminary biological testing revealed a significant analgesic activity of trifluoromethyl-containing antipyrine.