37613-13-1

Basic information

• Product Name: 3-(3?'-methylphenyl)-5-phenyl-1H-pyrazole
• Synonyms: 3-(3?'-methylphenyl)-5-phenyl-1H-pyrazole
• CAS NO: 37613-13-1
• Molecular Weight: 234.301
• Mol File: 37613-13-1.mol

Chemical Properties

• CAS DataBase Reference: 3-(3?'-methylphenyl)-5-phenyl-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3?'-methylphenyl)-5-phenyl-1H-pyrazole(37613-13-1)
• EPA Substance Registry System: 3-(3?'-methylphenyl)-5-phenyl-1H-pyrazole(37613-13-1)

Safety Data

• Hazardous Substances Data: 37613-13-1(Hazardous Substances Data)

Upstream product

• 16619-29-7 phenyl m-methylstyryl ketone 
• 53692-58-3 1-(3-methylphenyl)-3-phenylpropynone 
• 536-74-3 phenylacetylene 
• 1456785-10-6 3-amino-3-(3-methylphenyl)-1-phenylprop-2-en-1-one 
• 766-82-5 1-ethynyl-3-methyl-benzene 
• 698-16-8 benzohydroximoyl chloride 
• 620-23-5 m-tolyl aldehyde 
• 40154-50-5 C₁₅H₁₆N₂O₂S 

Relevant articles and documents

A facile and expeditious approach to substituted 1H-pyrazoles catalyzed by iodine

A facile and expeditious method for the synthesis of 1H-pyrazoles by the reaction of α,β-unsaturated aldehydes/ketones and sulfonyl hydrazide catalyzed by as low as 2 mol % I2 has been demonstrated. This synthetic system features simple operation and mild reaction conditions, and displays a broad functional group tolerance furnishing good to excellent yields.

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization

Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.

Sunlight-promoted Direct Irradiation of N-centred Anion: The Photocatalyst-free Synthesis of Pyrazoles in Water

A practical method through sunlight mediated annulation of α,β-unsaturated hydrazones has been developed for the synthesis of pyrazole. Based on the analysis of UV-Vis absorption of the substrate, the reaction was designed to avoid the use of external photocatalysis and proceeds via direct irradiation of N-centred anion by sunlight. The key features of this reaction include operational simplicity, readily available reagents, and amenability to gram-scale synthesis. (Figure presented.).

Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine

The reaction of terminal alkynes with n-BuLi, and then with aldehydes, followed by the treatment with molecular iodine, and subsequently hydrazines or hydroxylamine provided the corresponding 3,5-disubstituted pyrazoles or isoxazoles in good yields with high regioselectivity, through the formations of propargyl secondary alkoxides and α-alkynyl ketones. The present reactions are one-pot preparation of 3,5-disubstituted pyrazoles from terminal alkynes, aldehydes, molecular iodine, and hydrazines, and 3,5-disubstituted isoxazoles from terminal alkynes, aldehydes, molecular iodine, and hydroxylamine.

NOVEL COMPOUNDS

This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, Ar, R1, R2, R3 have meanings given in the description.

Copper on iron promoted one-pot synthesis of β-aminoenones and 3,5-disubstituted pyrazoles

The reaction of hydroximoyl chlorides with acetylenes in the presence of a copper on iron bimetallic system leads to β-aminoenones via reductive ring opening of isoxazole intermediates. The valuable β-aminoenone building blocks can be isolated or transformed into pyrazoles with the addition of hydrazine in a straightforward one-pot procedure.

An efficient one-pot synthesis of 3,5-disubstituted 1H-pyrazoles

An efficient, general, one-pot, three-component procedure for the preparation of 3,5-disubstituted 1H-pyrazoles via condensation of substituted aromatic aldehydes, tosylhydrazine and terminal alkynes in toluene is reported. The reaction tolerates a variety of functional groups and sterically hindered substrates to afford the desired pyrazoles in yields of 67-91%.