90861-52-2

Basic information

• Product Name: 5-METHYL-3-P-TOLYL-1H-PYRAZOLE
• Synonyms: 5-METHYL-3-P-TOLYL-1H-PYRAZOLE;SALOR-INT L232955-1EA;5-METHYL-3-(4-METHYLPHENYL)-1H-PYRAZOLE
• CAS NO: 90861-52-2
• Molecular Formula: C₁₁H₁₂N₂
• Molecular Weight: 172.23
• Mol File: 90861-52-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-METHYL-3-P-TOLYL-1H-PYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-3-P-TOLYL-1H-PYRAZOLE(90861-52-2)
• EPA Substance Registry System: 5-METHYL-3-P-TOLYL-1H-PYRAZOLE(90861-52-2)

Safety Data

• Hazardous Substances Data: 90861-52-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-METHYL-3-P-TOLYL-1H-PYRAZOLE is used as a building block in the synthesis of various biologically active compounds for pharmaceutical applications, leveraging its antitumor, anti-inflammatory, and antimicrobial properties to develop new drugs with therapeutic potential.
Used in Agrochemical Industry:
5-METHYL-3-P-TOLYL-1H-PYRAZOLE is used as a key intermediate in the development of agrochemicals, where its biological activities can contribute to the creation of effective pesticides, herbicides, or other agricultural chemicals to protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
5-METHYL-3-P-TOLYL-1H-PYRAZOLE is used as a versatile intermediate in organic synthesis, enabling the creation of a wide range of chemical compounds with various applications across different industries, from pharmaceuticals to materials science.

Upstream product

• 4023-79-4 1-(4-methylphenyl)butan-1,3-dione 
• 130649-66-0 1-(4-Methylphenyl)-3-buten-1-one 
• 1623809-05-1 C₁₈H₂₀N₂O₂S 
• 104-87-0 4-methyl-benzaldehyde 
• 4023-84-1 4-(p-tolyl)-3-buten-2-one 
• 104-85-8 para-methylbenzonitrile 
• 131474-81-2 (Z)-3-amino-1-(p-tolyl)but-2-en-1-one 
• 90861-41-9 (E)-3-(N'-Isopropylidene-hydrazino)-1-p-tolyl-but-2-enylideneamine 
• 93214-76-7 3-Methyl-5-p-tolyl-3,4-dihydro-2H-pyrazol-3-ol 
• 378186-93-7 1-(4-methylphenyl)-2,3-butadien-1-one 
• 122-00-9 para-methylacetophenone 
• 122851-98-3 1-(3-imino-1-methyl-3-p-tolylprop-1-enyl)-5-isothiocyanato-3-methyl-5-p-tolyl-2-pyrazoline 
• 93214-72-3 5-Methyl-3-p-tolyl-3,4-dihydro-2H-pyrazol-3-ol 

Downstream Products

• 1430100-72-3 1-(3'-phenylquinoxalin-2'-yl)-3-(4-methylphenyl)-5-methylpyrazole 
• 1000189-53-6 1-(3'-methylquinoxalin-2'-yl)-3-methyl-5-(4-methylphenyl)pyrazole 
• 1000189-54-7 1-(3'-methylquinoxalin-2'-yl)-3-(4-methylphenyl)-5-methylpyrazole 
• 1173169-36-2 C₂₅H₁₉N₃O₂ 

Relevant articles and documents

Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors

Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.

Monohydrochloride Assisted Synthesis of Functionalized Isoxazoles and Pyrazoles from Allenic Ketones: First Synthesis of (Z)-2-Methyl-7H-benzo[b]pyrazolo[5,1-d][1,5]oxazocines

A facile hydrochloride promoted regioselective synthesis of isoxazoles and pyrazoles from 1,2-allenic ketones is reported. The reaction has been scaled up to gram scale. A direct 8-endo dig ring annulations towards the first synthesis of (Z)-2-methyl-7H-b

Design, synthesis and biological evaluation of novel hydroxamic acid based histone deacetylase 6 selective inhibitors bearing phenylpyrazol scaffold as surface recognition motif

In recent years, inhibition of HDAC6 became a promising therapeutic strategy for the treatment of cancer and HDAC6 inhibitors were considered to be potent anti-cancer agents. In this work, celecoxib showed moderate degree of HDAC6 inhibition activity and selectivity in preliminary enzyme inhibition activity assay. A series of hydroxamic acid derivatives bearing phenylpyrazol moiety were designed and synthesized as HDAC6 inhibitors. Most compounds showed potent HDAC6 inhibition activity. 11i was the most selective compound against HDAC6 with IC50 values of 0.020 μM and selective factor of 101.1. Structure-activity relationship analysis indicated that locating the linker group at 1′ of pyrazol gave the most selectivity. The most compounds 11i (GI50 = 3.63 μM) exhibited 6-fold more potent than vorinostat in HepG2 cells. Considering of the high selectivity against HDAC6 and anti-proliferation activity, such compounds have potential to be developed as anti-cancer agents.

Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof

The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.

Photocatalytic Generation of N-Centered Hydrazonyl Radicals: A Strategy for Hydroamination of β,γ-Unsaturated Hydrazones

A visible-light photocatalytic generation of N-centered hydrazonyl radicals has been accomplished for the first time. This approach allows efficient intramolecular addition of hydrazonyl radical to terminal alkenes, thus providing hydroamination and oxyamination products in good yields. Importantly, the protocol involves deprotonation of an N-H bond and photocatalytic oxidation to an N-centered radical, thus obviating the need to prepare photolabile amine precursors or the stoichiometric use of oxidizing reagents.

A simple and efficient synthesis of pyrazoles in water

A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups, Aromatic moiety with both electron-rich and electron-deficient substituents could give desired products in good to excellent yields.

A regioselective synthesis of some new pyrazol-1′-ylpyrazolo[1,5-a] pyrimidines in aqueous medium and their evaluation as antimicrobial agents

An efficient and environmental benign regioselective synthesis of some new pyrazol-1′-ylpyrazolo[1,5-a]pyrimidines (7b-h) has been accomplished via treatment of 3(5)-amino-5(3)-hydrazinopyrazole dihydrochloride (5) with several unsymmetrical 1,3-diketones (6b-h) using water as a solvent without any catalysts or additives. The structure of 7b-h was established on the basis of rigorous analysis of 1H, 13C NMR, IR spectral data and MS. Eight compounds (7a-h) were screened for their antibacterial activity against two gram-positive and two gram-negative bacteria and compounds (7a, b, d and e) for antifungal activity against four phytopathogenic fungi. Compounds 7c and 7e manifest rather broad antibacterial activity than standard antibiotics. One lead compound, 7a (10 mg/ml and 200 mg/ml) exhibited equipotent or more potent antifungal activity against all tested microorganisms than standard drug.

Reactivity of p-Phenyl Substituted β-Enamino Compounds using K-10/ultrasound. I. Synthesis of Pyrazoles and Pyrazolinones

The reactivity of the β-enamino ketones, 3-amino-l-(p-phenyl-substituted)-2-buten-l-ones la-d and β-enamino esters. Ethyl-3-amino-3-(p-phenyl-substituted)-2-propenoates 5a-d were evaluated by systematic studies of the reactions with hydrazine and methylhydrazine by reactions with solid support K-10/ultrasound and homogeneous media (reflux in ethanol or dichloromethane) yielding pyrazole rings 2a-d, Af-methylpyrazoles 3a-d, 4a-d and N-methylpyrazolinones 6a-c and 7a-c. The regiochemistry of the cyclization showed dependence of the reaction conditions employed as well as the substituent in the aromatic ring.

Reactivity of p-phenyl substituted β-enamino compounds using K- 10/ultrasound. I. Synthesis of pyrazoles and pyrazolinones

The reactivity of the β-enamino ketones, 3-amino-1-(p-phenyl- substituted)-2-buten-1-ones 1a-d and β-enamino esters, ethyl 3-amino-3-(p- phenyl-substituted)-2-propenoates 5a-d was systematically studied when allowed to react with hydrazine and methylhydrazine under solid support K- 10/ultrasound conditions and in homogeneous media (reflux in ethanol or dichloromethane). The products were pyrazoles 2a-d, N-methylpyrazoles 3a-d, 4a-d and N-methylpyrazolinones 6a-c and 7a-c. The regiochemistry of the cyclization reactions showed dependence upon the reaction conditions employed as well as upon the substituent in the aromatic ring.

SYNTHESIS AND REARRANGEMENT OF 5-ISOTHIOCYANATOPYRAZOLINES

1-(3-Iminoprop-1-enyl)-5-isothiocyanato-2-pyrazolines have been synthesized by reaction of hydrazine derivatives with carbon disulfide.These pyrazoline derivatives are precursors of pyrimidinylpyrazoles.