100553-83-1

Basic information

• Product Name: 2-(4-Chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazole-3-one
• Synonyms: 1-(4-Fluorophenyl)-3-methyl-2-pyrazolin-5-one;1-(4-Fluorophenyl)-3-methyl-4,5-dihydropyrazole-5-one;2-(4-fluorophenyl)-2,4-dihydro-5-methyl-3H-Pyrazol-3-one;1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5(4H)-one;2-(4-fluorophenyl)-5-methyl-4H-pyrazol-3-one;1-(4-fluorophenyl)-3-methyl-4,5-dihydro-1H-pyrazol-5-one
• CAS NO: 100553-83-1
• Molecular Formula: C₁₀H₉FN₂O
• Molecular Weight: 192.19
• Mol File: 100553-83-1.mol

Chemical Properties

• Melting Point: 148-149℃
• Boiling Point: 351.3 °C at 760 mmHg
• Flash Point: 166.3 °C
• Appearance: /
• Density: 1.26
• Vapor Pressure: 4.15E-05mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 2-(4-Chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazole-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazole-3-one(100553-83-1)
• EPA Substance Registry System: 2-(4-Chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazole-3-one(100553-83-1)

Safety Data

• Hazardous Substances Data: 100553-83-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazole-3-one was initially used as an anti-inflammatory agent for the treatment of conditions such as osteoarthritis, rheumatoid arthritis, and menstrual pain. Its application was based on its ability to selectively inhibit the COX-2 enzyme, which is involved in the production of prostaglandins that cause inflammation and pain.
Used in Drug Development Research:
Despite its withdrawal from the market, 2-(4-Chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazole-3-one continues to be studied for its potential therapeutic uses and applications in drug development. Researchers are exploring modifications to its chemical structure to improve its safety profile and develop new drugs with similar anti-inflammatory properties but with fewer side effects. This ongoing research may lead to the discovery of safer and more effective NSAIDs in the future.

InChI:InChI=1/C10H9FN2O/c1-7-6-10(14)13(12-7)9-4-2-8(11)3-5-9/h2-5H,6H2,1H3

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 371-14-2 4-fluorophenylhydrazine 
• 674-82-8 4-methyleneoxetan-2-one 
• 141-97-9 ethyl acetoacetate 
• 371-40-4 4-fluoroaniline 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 

Downstream Products

• 1426835-16-6 6-fluoro-3-((1-(4-fluorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(4-methoxyphenyl)methyl)chroman-2,4-dione 
• 1426835-13-3 3-((1-(4-fluorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(4-hydroxy-3-methoxyphenyl)methyl)chroman-2,4-dione 
• 377767-11-8 C₁₁H₈ClFN₂O 
• 926190-52-5 C₁₁H₈ClFN₂O₂ 

Relevant articles and documents

Catalytic System-Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones

A catalytic system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N?N bond activation/[n+1] annulation cascade, a C(sp2)-H activation/[4+1] annulation and a novel tandem C(sp2)-H/C(sp3)?H bond activation/[4+1] annulation strategy, along with a broad scope of substrates, moderate to excellent yields and valuable transformations. More importantly, in these transformations, we are the first time to capture a N?N bond activation and a C(sp3)?H bond activation of pyrazolidinones under different catalytic system.

The selective condensation of pyrazolones to isatins in aqueous medium

The selective condensation of pyrazolones with isatins using water as the reaction medium is presented. This strategy provides an environmentally benign synthetic route to synthesize various potentially bioactive pyrazolone substituted oxindoles.

Design, synthesis and biological evaluation of novel pyrazole sulfonamide derivatives as potential AHAS inhibitors

Acetohydroxy acid synthase (AHAS; EC 2.2.1.6, also referred to as acetolactate synthase, ALS) has been considered as an attractive target for the design of herbicides. In this work, an optimized pyrazole sulfonamide base scaffold was designed and introduced to derive novel potential AHAS inhibitors by introducing a pyrazole ring in flucarbazone. The results of in vivo herbicidal activity evaluation indicates compound 3b has the most potent activity with rape root length inhibition values of 81percent at 100 mg/L, and exhibited the best inhibitory ability against Arabidopsis thaliana AHAS. With molecular docking, compound 3b insert into Arabidopsis thaliana AHAS stably by an H-bond with Arg377 and cation-p interactions with Arg377, Trp574, Tyr579. This study suggests that compound 3b may serve as a potential AHAS inhibitor which can be used as a novel herbicides and provides valuable clues for the further design and optimization of AHAS inhibitors.

Discovery of novel double pyrazole Schiff base derivatives as anti-tobacco mosaic virus (TMV) agents

Many pyrazole derivatives were reported to exhibit highly activity towards tobacco mosaic virus (TMV). In this work, an optimized pyrazole Schiff base scaffold was designed and introduced to derive novel potential TMV inhibitors. Thirty-six compounds were synthesized, characterized by elemental analysis, mass spectra and nuclear magnetic resonance (NMR) spectroscopy and evaluated by biological experiments. The bioassay results showed that some of the synthesized compounds exhibited excellent anti-TMV activities. Especially, 5-chloro-3-methyl-1H-pyrazole contained compound 4j showed ningnanmycin comparable inhibitory activity and can be considered as potential anti-TMV candidate agent. With molecular docking, compound 4j insert into nucleotide sequence (GAAGUU) of OriRNA stably which revealed nucleotide could be a target of these compounds.

Preparation and Antibacterial Activity of 3-Methyl-1-p-substituted Phenylpyrazole-5-thiol

3-Methyl-1-phenylpyrazole-5-thiol (3a) and its p-nitro- (5) and p-fluorophenyl (8) derivatives were prepared as potential antimicrobial agents in relatively good yields. Compounds 3a and 8 showed good antibacterial activities against MRSA, S. aureus, S. epidermidis, E. faecalis, E.faecium, and S. pyogenes. Moreover, compound 3a also showed a synergistic effect with some aminoglycosides.

Discovery of novel triazole-containing pyrazole ester derivatives as potential antibacterial agents

To develop new antibacterial agents, a series of novel triazole-containing pyrazole ester derivatives were designed and synthesized and their biological activities were evaluated as potential topoisomerase II inhibitors. Compound 4d exhibited the most potent antibacterial activity with Minimum inhibitory concentration (MIC) alues of 4 μg/mL, 2 μg/mL, 4 μg/mL, and 0.5 μg/mL against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella gallinarum, respectively. The in vivo enzyme inhibition assay 4d displayed the most potent topoisomerase II (IC50 = 13.5 μg/mL) and topoisomerase IV (IC50 = 24.2 μg/mL) inhibitory activity. Molecular docking was performed to position compound 4d into the topoisomerase II active site to determine the probable binding conformation. In summary, compound 4d may serve as potential topoisomerase II inhibitor.

Diversity-Oriented Synthesis of Spiropentadiene Pyrazolones and 1 H-Oxepino[2,3- c]pyrazoles from Doubly Conjugated Pyrazolones via Intramolecular Wittig Reaction

An efficient method for the diversity-oriented synthesis of spiropentadiene pyrazolones and 1H-oxepino[2,3-c]pyrazoles is reported. The methodology attributes O-acylation of phosphorus zwitterions which were formed by a tandem phospha-1,6-addition of PBu3 to α,β,γ,δ-unsaturated pyrazolones, further generating betaine intermediates that preferentially resulted in the aforementioned cyclic products in a diversity-oriented manner. The mechanistic investigations revealed that formation of the betaines is the key step to provide the products via an intramolecular Wittig reaction or an unprecedented δ-C-acylation/cyclization/Wittig reaction.

Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions

An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product could be afforded without silica gel column purification. In addition, the prepared ammonium oxides are versatile building blocks for synthesizing functionalized pyrazole derivatives.

Enantioselective Synthesis of Spiropyrazolone-Fused Cyclopenta[ c]chromen-4-ones Bearing Five Contiguous Stereocenters via (3+2) Cycloaddition

An enantioselective synthesis of spiropyrazolone-fused cyclopenta[c]chromen-4-ones is demonstrated via a (3+2) cycloaddition reaction. The reactions of 3-homoacylcoumarins and α,β-unsaturated pyrazolones in the presence of the cinchona-alkaloid derived hy

Rhodium-Catalyzed [4+2] Annulation of N-Aryl Pyrazolones with Diazo Compounds To Access Pyrazolone-Fused Cinnolines

An efficient synthesis of novel dinitrogen-fused heterocycles such as pyrazolo[1,2-a]cinnoline derivatives have been accomplished by the rhodium(III)-catalyzed reaction of N-arylpyrazol-5-ones with α-diazo compounds. This reaction proceeds through a cascade C?H activation/intramolecular cyclization with a broad substrate scope. Furthermore, this protocol is successfully extended to the unusual phosphorus-containing α-diazo compounds and cyclic diazo compounds as the cross-coupling partners to deliver the two new kinds of pyrazolo[1,2-a]cinnolinones. The control experiments were performed to reveal insight into the mechanism of this reaction, involving reversible C?H activation, migratory insertion of the diazo compound, and cascade cyclization as the key steps of the transformation. Moreover, gram-scale synthesis and further transformation of the target product demonstrate the synthetic utility of the present protocol.