19735-89-8

Basic information

• Product Name: 1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one
• Synonyms: 1,2-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-one;1-PHENYL-3-METHYL-5-PYRAZOLONE;5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one;1-Phenyl-3-methyl-1H-pyrazole-5(2H)-one;2-Phenyl-5-methyl-1,2-dihydro-3H-pyrazole-3-one;2-Phenyl-5-methyl-1H-pyrazole-3(2H)-one;5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazole-3-one;1,2-Dihydro-5-methyl
• CAS NO: 19735-89-8
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• EINECS: 243-261-8
• Mol File: 19735-89-8.mol

Chemical Properties

• Melting Point: 128°C
• Boiling Point: 305.17°C (rough estimate)
• Flash Point: 120.991 °C
• Appearance: /
• Density: 1.2600
• Vapor Pressure: 0.0048mmHg at 25°C
• Refractive Index: 1.6370 (estimate)
• PKA: 0.10±0.40(Predicted)
• CAS DataBase Reference: 1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one(19735-89-8)
• EPA Substance Registry System: 1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one(19735-89-8)

Safety Data

• Hazardous Substances Data: 19735-89-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one is used as a research compound for studying its chemical properties and potential applications in various fields. Its heterocyclic structure and the possibility of functional group modifications make it an interesting subject for scientific investigation.
Used as a Potential Bioactive Agent:
Due to its unique structure and properties, 1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one is considered a potential bioactive agent. It may have applications in the development of new drugs or therapeutic agents, given its ability to interact with biological systems. Further research is needed to explore its potential in this area and to understand its mechanism of action.

InChI:InChI=1/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,11H,1H3

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 67790-05-0 3-phenylhydrazono-butyric acid-(N'-phenyl-hydrazide) 
• 100-63-0 phenylhydrazine 
• 27349-35-5 5-methoxy-3-methyl-1-phenyl-1H-pyrazole 
• 1016-41-7 5-ethoxy-3-methyl-1-phenyl-1H-pyrazole 
• 35467-82-4 ethyl 3-(phenylazo)but-2-enoate 
• 6078-46-2 ethyl 3-(2-phenylhydrazono)butanoate 
• 74-87-3 methylene chloride 
• 55774-20-4 1-benzyl-5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 
• 124559-22-4 3-phenylhydrazono-butyric acid anilide 
• 15900-11-5 (5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-4-ylidene)-methane 
• 59-88-1 phenylhydrazine hydrochloride 
• 141-97-9 ethyl acetoacetate 
• 114-83-0 1-acetyl-2-phenylhydrazine 

Downstream Products

• 27349-35-5 5-methoxy-3-methyl-1-phenyl-1H-pyrazole 
• 60-80-0 antipyrine 
• 56159-67-2 (3-methyl-1-phenyl-1H-pyrazol-5-yl) benzoate 
• 108852-08-0 5-methyl-2-phenyl-4-pyrrol-2-ylmethylene-2,4-dihydro-pyrazol-3-one 
• 109733-46-2 5-methyl-2-phenyl-4-[(4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-methyl]-1,2-dihydro-pyrazol-3-one 
• 103207-52-9 5-methyl-2-phenyl-4-[(4-phenyl-thiazol-2-ylamino)-methyl]-1,2-dihydro-pyrazol-3-one 
• 57784-82-4 4-(1-amino-ethylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 397878-11-4 5,5'-dimethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-benzylidene-bis-pyrazol-3-one 
• 15900-11-5 (5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-4-ylidene)-methane 
• 172038-40-3 5,5'-dimethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-methanediyl-bis-pyrazol-3-one 
• 103505-79-9 5-methyl-4-[(4-phenethyl-thiazol-2-ylamino)-methyl]-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 16335-66-3 1-phenyl-3-methyl-4-(2-methoxy-phenylhydrazo)-5-pyrazolone 
• 97032-57-0 5-(5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylmethylene)-pyrimidine-2,4,6-trione 
• 19205-04-0 5-methyl-2-phenyl-2H-pyrazole-3,4-dione 4-[(3-methyl-3H-benzothiazol-2-ylidene)-hydrazone] 

Relevant articles and documents

RECYCLIZATION OF 4-METHYL(PHENYL)-2,3-DIHYDRO-1H-1,5-BENZODIAZEPIN-2-ONES

Depending on the reaction conditions, the hydrazinolysis of 4-(acetyl-methylene)-1,2,3,5-tetrahydro-1,5-benzodiazepin-2-one affords N-(2-aminophenyl)-5-methyl-3-pyrazolylacetamide or 2-benzimidazo-5-methyl-3-pyrazolylmethane.In the presence of phenylhydrazine, 3,4,5-trimethyl-1,5-benzodiazepine is recyclized to 3,4,5-trimethyl-1-phenyl-2-pyrazole.

2-(3-Methyl-1-phenyl-1 H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones as potent antioxidant and antidiabetic agent

A series of 2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones (7a-7j) were synthesized by intramolecular cyclization of imines (6a-6j) with thioglycolic acid in the presence of acid catalyst. The Schiff bases were obtained upon reaction between electrophilic carbon atom of 3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (4) and nucleophilic nitrogen atom of substituted aromatic amines. in vitro Antioxidant activity was determined by DPPH redical scavenging assay mehod using ascorbic acid as standard. The antidiabetic activity was carried out by streptazocine induced diabetic method using rosiglitazone as standard drug on wister rats. From the study it were found that 3-(4-chlorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7a), 3-(4-bromophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7b), 3-(3,4-dichlorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7d ), 3-(3,4-difluorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7f) 2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-(trifluoromethyl) phenyl) thiazolidin-4-one (7h), 3-(4-methoxyphenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl) thiazolidin-4-one (7j) shown more IC50compare to standard. Where as compound 7a, 7b, 7h, 7j show more significant antidiabetic effect against hyperglycemic rats compare to standard drugs at the dose of 5 mg/kg after 21 days of treatment.

Design and Synthesis of Fused and Spiro Pyrazole Derivatives

Abstract: Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with p-hydroxybenzaldehyde in alcoholic sodium hydroxide yielded (Z)-4-(4-hydroxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one which was treated with acetylacetone, hydrazine hydrate, ethyl cyanoacetate, and ethyl acetoacetate to afford pyranopyrazole, pyrazolopyrazole, pyrazolopyridine, and 6-aminopyrazolopyridine derivatives, respectively. 5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one was also reacted at the enamino carbon atom with 2,4-dichlorobenzoyl isothiocyanate, thiosemicarbazide, and hydrazine hydrate to produce pyrazolooxazine, pyrazolopyrazole, and spiro[pyrazole-3,3′-pyrazolo[3,4-c]pyrazole] derivatives.

Structures and chemical equilibria of some N-heterocycles containing amide linkages

Structures and chemical equilibria of 5-carboxy-2-thiouracil (1), 5,6-diphenyl-3-hydroxy-1,2,4-triazine (2), 1-phenyl-3-methyl-5-pyrazolone (3) and 2-mercapto-4,6-dimethylpyrimidine hydrochloride (4) are reported. Their electronic transitions are assigned and pK values are evaluated and discussed.

Synthesis of Pyrano, Pyrido, Oxazino, and Spiro Pyrazole Derivatives and Their Antimicrobial Activity

Abstract: Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with 4-hydroxybenzaldhyde in alcoholic sodium hydroxide yielded 4-(4-hydroxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and treatment of the latter with acetylacetone, hydrazine hydrate, ethyl cyanoacetate, and ethyl acetoacetate gave pyranopyrazole, pyrazolopyrazole, and pyrazolopyridine derivatives. 5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one was reacted with 2,4-dichlorobenzoyl isothiocyanate, thiosemicarbazide, and hydrazine hydrate to afford pyrazolooxazine, pyrazolopyrazole, and spiro[pyrazole-3,3′-pyrazolo[3,4-c]pyrazole] derivatives. Some of the newly synthesized compounds showed high antimicrobial activity against three microbial strains (S. aureus, E. coli, C. albicans).

Ligand based design and synthesis of pyrazole based derivatives as selective COX-2 inhibitors

The design and synthesis of novel pyrazole based derivatives has been carried out using the ligand based approach like pharmacophore and QSAR modelling of reported pyrazoles from the available literature to investigate the chemical features that are essential for the design of selective and potent COX-2 inhibitors. Both pharmacophore and QSAR models with good statistical parameters were selected for the design of the lead molecule. Also by exploiting the chemical structures of selective and marketed COX-2 inhibitors, celecoxib and SC-558 were used in designing the molecules which are used in the treatment of inflammation and related disorders. The therapeutic action of the Non-Steroidal Anti-inflammatory Agents (NSAIDs) is based primarily on the COX-2 inhibition. With this background we have synthesized some azomethine derivatives of 3-methyl-1-substituted-4-phenyl-6-[{(1E)-phenylmethylene}amino]-1,4-dihydro pyrano[2,3-c]pyrazole-5-carbonitrile 6(a-o) and were characterized by 1HNMR, 13CNMR and Mass spectral techniques. All the synthesized pyrazole derivatives were tested for in vitro membrane stability property in both COX-1 & COX-2 inhibition studies and in vivo anti-inflammatory activity by carrageenan induced rat paw edema model. Among them, compound 6k showed very good activity by in vivo anti-inflammatory activity with 0.8575 mmol/kg as ED50. Similarly compounds 6m, 6o, 6i and 6h exhibited comparable anti-inflammatory activity to standard drugs. Also the active compounds were further screened for ulcerogenic activity and were found be safer with less ulcer index compared to the marketed drugs like aspirin, ibuprofen and celecoxib.

Copper-catalyzed convenient synthesis and SAR studies of substituted-1,2,3-triazole as antimicrobial agents

Background: A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent. Objective: We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity. Methods: A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively. Results and Conclusion: From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

Efficient Synthesis of Five Types of Heterocyclic Compounds via Intramolecular Elimination Using Ultrasound-Static Heating Technique

An experimental technique, ultrasound-static heating, has been developed for the efficient synthesis of heterocyclic compounds. The technique involves ultrasonic irradiation and static heating processes. First, the ultrasonic irradiation process is performed to form an intermediate of the heterocyclic compound under mild conditions and the subsequent static heating process (heating the intermediate under solvent-free conditions without stirring) produces the target heterocyclic compounds via intramolecular elimination.

Cobalt doped ZnS nanoparticles as a recyclable catalyst for solvent-free synthesis of heterocyclic privileged medicinal scaffolds under infrared irradiation

This paper reports preparation and characterization of cobalt doped ZnS NPs and their catalytic application in the synthesis of heterocyclic privileged medicinal scaffolds involving pyrazolones (with excellent regioselectivity) and 1,3-oxathiolan-5-one frameworks under infrared irradiation. Nanoparticles have been prepared at room temperature by a wet chemical method. The heterogeneous catalysts were fully characterized by XRD, TEM, EDAX, ICP-AES and UV/Vis. Under infrared radiation (IR), the catalytic activity of Co doped ZnS NPs was about 40-fold higher under IR as compared to the conventional method. Nanocatalyst plays a dual role of catalyst as well as susceptor, and enhances the overall capacity to absorb IR in the reaction mixture. Doping by Co promotes the activity and selectivity of ZnS NPs as indicated by their high TOF value, providing the products with good to excellent yields. The surface acidity of NPs was measured by FTIR spectra of chemisorbed pyridine. The present method does not involve any hazardous organic solvent or catalyst. The introduction of nanocatalyst in an IR system offers promising features for the reaction response such as the shorter reaction time, simple work-up procedure, and purification of products by non-chromatographic methods. The catalyst was reused up to four runs without an appreciable loss of catalytic activity.

Synthesis and biological evaluation of substituted pyrazoles as blockers of divalent metal transporter 1 (DMT1)

Three distinct series of substituted pyrazole blockers of divalent metal transporter 1 (DMT1) were elaborated from the high-throughput screening pyrazolone hit 1. Preliminary hit-to-lead efforts revealed a preference for electron-withdrawing substituents in the 4-amido-5-hydroxypyrazole series 6a-l. In turn, this preference was more pronounced in a series of 4-aryl-5- hydroxypyrazoles 8a-j. The representative analogs 6f and 12f were found to be efficacious in a rodent model of acute iron hyperabsorption. These three series represent promising starting points for lead optimization efforts aimed at the discovery of DMT1 blockers as iron overload therapeutics.