10250-60-9

Basic information

• Product Name: 1,5-dimethyl-3-phenylpyrazole
• Synonyms: 1,5-dimethyl-3-phenylpyrazole
• CAS NO: 10250-60-9
• Molecular Formula: C₁₁H₁₂N₂
• Molecular Weight: 172.23
• Mol File: 10250-60-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 281.7°Cat760mmHg
• Flash Point: 124.2°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 0.00599mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: 1,5-dimethyl-3-phenylpyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-dimethyl-3-phenylpyrazole(10250-60-9)
• EPA Substance Registry System: 1,5-dimethyl-3-phenylpyrazole(10250-60-9)

Safety Data

• Hazardous Substances Data: 10250-60-9(Hazardous Substances Data)

Usage

Chemical structure

Pyrazole derivative with two methyl groups and a phenyl group attached to the pyrazole ring

Usage

Organic synthesis and medicinal chemistry

Building block

Production of various pharmaceutical drugs and agrochemicals

Biological activities

Exhibits potential anti-inflammatory and anti-cancer properties

Applications

Development of dyes, pigments, and materials science

Unique properties

Versatile uses and significant role in chemistry and biochemistry

InChI:InChI=1/C11H12N2/c1-9-8-11(12-13(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3

Upstream product

• 98-88-4 benzoyl chloride 
• 6710-62-9 1-phenyl-2-butyn-1-one 
• 60-34-4 methylhydrazine 
• 13061-96-6 dihydroxy-methyl-borane 
• 33093-76-4 3,3-dibromo-1-phenylprop-2-en-1-one 
• 57-14-7 N,N-Dimethylhydrazine 
• 95514-24-2 (Z)-1-amino-1-phenyl-1-buten-3-one 
• 23652-90-6 (2Z)-3-amino-1-phenylbut-2-en-1-one 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 64-17-5 ethanol 
• 93-91-4 1-phenylbutan-1,3-dione 
• 60-29-7 diethyl ether 
• 77252-92-7 3-ethoxy-1-phenyl-but-2-en-1-one 

Downstream Products

• 26565-49-1 1,2,3-trimethyl-5-phenyl-pyrazolium; iodide 
• 1607827-11-1 4-(1,5-dimethyl-3-phenyl-1H-pyrazol-4-yl)morpholine 

Relevant articles and documents

DPD-Inspired Discovery of Novel LsrK Kinase Inhibitors: An Opportunity to Fight Antimicrobial Resistance

Antibiotic resistance is posing a continuous threat to global public health and represents a huge burden for society as a whole. In the past decade, the interference with bacterial quorum sensing (QS) (i.e., cell-cell communication) mechanisms has extensively been investigated as a valid therapeutic approach in the pursuit of a next generation of antimicrobials. (S)-4,5-Dihydroxy-2,3-pentanedione, commonly known as (S)-DPD, a small signaling molecule that modulates QS in both Gram-negative and Gram-positive bacteria, is phosphorylated by LsrK, and the resulting phospho-DPD activates QS. We designed and prepared a small library of DPD derivatives, characterized by five different scaffolds, and evaluated their LsrK inhibition in the context of QS interference. SAR studies highlighted the pyrazole moiety as an essential structural element for LsrK inhibition. Particularly, four compounds were found to be micromolar LsrK inhibitors (IC50 ranging between 100 μM and 500 μM) encouraging further exploration of novel analogues as potential new antimicrobials.

The preparation of substituted pyrazoles from β,β-dibromo-enones by a tandem condensation/Suzuki-Miyaura cross-coupling process

Two consecutive tandem processes are described for the regioselective, two-step synthesis of 1,3,5-trisubstituted pyrazoles from α- hydroxyketones. The first, a tandem MnO2-mediated oxidation/Ramirez olefination reaction, provides a facile route to β,β-dibromo-enones. These valuable 1,3-dicarbonyl synthons can then be converted into 1,3,5-trisubstituted pyrazoles via a second tandem hydrazine condensation/Suzuki-Miyaura cross-coupling reaction. Using these procedures, a range of aryl and alkyl α-hydroxyketones have been transformed regioselectively into 1,3,5-trisubstituted pyrazoles. Georg Thieme Verlag Stuttgart.

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.