34347-81-4

Basic information

• Product Name: 1-Methyl-3-phenyl-1H-pyrazol-5-ol
• Synonyms: 2,4-Dihydro-2-methyl-5-phenyl-3H-pyrazol-3-one;1-METHYL-3-PHENYL-1H-PYRAZOL-5-OL;2-methyl-5-phenyl-1H-pyrazol-3-one
• CAS NO: 34347-81-4
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• Mol File: 34347-81-4.mol

Chemical Properties

• Melting Point: 213-215°C
• Boiling Point: 294.4 °C at 760 mmHg
• Flash Point: 131.9 °C
• Appearance: /
• Density: 1.178 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: 2-8°C
• PKA: 8.86±0.28(Predicted)
• CAS DataBase Reference: 1-Methyl-3-phenyl-1H-pyrazol-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-phenyl-1H-pyrazol-5-ol(34347-81-4)
• EPA Substance Registry System: 1-Methyl-3-phenyl-1H-pyrazol-5-ol(34347-81-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 34347-81-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-3-phenyl-1H-pyrazol-5-ol is used as a potential anti-inflammatory and analgesic agent for its ability to reduce inflammation and alleviate pain. Its potential in this application is supported by studies that have shown its efficacy in these areas, although further research is necessary to confirm its therapeutic potential and safety profile.
Used in Neuroprotection Research:
MPP is used as a subject of investigation in neuroprotection, with research exploring its potential to protect neurons from damage and degeneration. This application is significant in the context of developing treatments for neurodegenerative diseases, where neuroprotective agents could play a crucial role in managing or slowing disease progression.
Used in Treatment of Neurodegenerative Diseases:
1-Methyl-3-phenyl-1H-pyrazol-5-ol is considered for use as a potential treatment for neurodegenerative diseases due to its demonstrated neuroprotective properties. The exploration of MPP in this context is based on its ability to potentially mitigate the effects of such conditions by protecting neuronal cells and supporting their function. Further studies are required to fully understand its effectiveness and safety in this application.

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

Upstream product

• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 60-34-4 methylhydrazine 
• 22038-72-8 methyldiazene 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 98-86-2 acetophenone 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 

Downstream Products

• 400073-98-5 C₁₈H₁₆N₂O₂ 
• 109925-44-2 C₁₇H₁₃ClN₂O₂ 
• 191419-15-5 5-chloro-1-methyl-3-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 191419-14-4 5-chloro-1-methyl-3-phenyl-1H-pyrazole-4-carboxylic acid 
• 318233-98-6 1-methyl-3-phenyl-5-p-tolylsulfanyl-1H-pyrazole-4-carbaldehyde 
• 929634-74-2 5-(furan-2-ylmethylsulfanyl)-1-methyl-3-phenyl-1H-pyrazole-4-carbaldehyde 

Relevant articles and documents

New hydrazone derivatives of pyrazole-4-carboxaldehydes exhibited anti-inflammatory properties

Background: Several series of hydrazone derivatives of pyrazole-4-carboxaldehydes (4-11) were designed and synthesized to screen their inflammatory activity. Methods: The products were characterized by1H NMR,13C NMR and HRMS. In vitro LPS-induced TNF-α model and in vivo xylene-induced ear-edema model were used to evaluate their anti-inflammatory activity. Results and Conclusion: Bioassays indicated that most of the compounds markedly inhibited the expression of TNF-α at the concentration of 10 μg/mL. Compounds 7b and 11c, two of the most potent compounds, exhibited TNF-α inhibitory ability in a dose-dependent manner with IC50 values of 5.56 and 3.69 μM, respectively. In vivo, intraperitoneal administration with 7b and 11c markedly inhibited the ear edema at the doses of 20 and 50 mg/kg. Compound 11c, inhibited edema by 49.59 % at the dose of 20 mg/kg, was comparable to the reference drug dexamethasone at the same dose (with an inhibition of 50.49 %). To understand the binding pattern, molecular docking of representa-tive 7b and 11c was performed, which demonstrated that both compounds have a forceful binding with the TNF-α, and that the phenyl and hydrazide moieties of them play a significant role in binding with the target site.

Synthesis and biological evaluation of pyrimidine derivatives as novel human Pin1 inhibitors

Pin1 (Protein interacting with NIMA1) is a cis–trans isomerase and promotes the amide bond rotation of phosphoSer/Thr-Pro motifs in its substrates. Inhibition of Pin1 might be a novel strategy for developing anticancer agents. Herein, a series of pyrimidi

Synthesis and evaluation of anticonvulsant activities of pyrazol semicarbazones. Part II

A series of 2-((5-aryloxy-1-methyl-3-methyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (6a-6l) and 2-((5-aryloxy-1-methyl-3-phenyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (7a-7l) were designed and synthesized. The maximal electroshock shock (MES) and subcutaneous pentylenetetrazole (sc-PTZ) seizure models in mice were used to evaluate the antiepileptic effect of compounds synthesized. Further, the acute neurotoxicity profile was also studied via the rotarod test. The results of sc-PTZ test indicate that a majority of compounds possessed anticonvulsant activity with long duration of protection effects. Among of them, compound 6k was found to be the most promising one, with an ED50 value of 20.4 mg/kg (in sc-PTZ model) and a PI value of 10.8, possessing higher anti-PTZ activity and wider safety margin than valproate and ethosuximide.

Synthesis and biological activity of new (E)-α-(Methoxyimino) benzeneacetate derivatives containing a substituted pyrazole ring

Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with high activity, a series of new strobilurin derivatives containing a substituted pyrazole in the side chain were synthesized and their biological activities were tested. The compounds were identified by 1H nuclear magnetic resonance, infrared, and elemental analysis. The test results indicated that the compounds exhibited strong fungicidal activities against Pyricularia oryzae, Phytophthora infestans, Pseudoperonospora cubenssi, and Erysiphe graminis. The relationship between structure and biological activity is discussed in terms of the effects of the substituents on the pyrazole ring. The present work demonstrates that strobilurin analogues with a 3-(substituted phenyl)-1 H-pyrazol-5-oxy side chain can be used as possible lead compounds for the development of potential agrochemicals.

5-((1H-Pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one inhibitors of ADAMTS-5

A series of 5-((1H-pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one inhibitors of ADAMTS-5 (aggrecanase-2) is described. These compounds show μM functional inhibition of ADAMTS-5, and represent a new class of agents with the potential of inhibiting degradation of aggrecan, a major component of cartilage which is lost in osteoporosis. Compound 12 is noteworthy in that it has an ADAMTS-5 IC50: 1.1 μM and shows >40-fold functional selectivity over ADAMTS-4 (aggrecanase-1).

Cyclocondensation of Alkylhydrazines and β-Substituted Acetylenic Esters: Synthesis of 3-Hydroxypyrazoles

Addition of monosubstituted alkylhydrazines to acetylenic esters with either electron-withdrawing or sterically bulky β-substituents afforded 1-alkyl-3-hydroxy-5-substituted-pyrazoles 1 as the major regioisomeric product.By comparison, the classical cyclo