761446-45-1

Basic information

• Product Name: 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester
• Synonyms: 1-BENZYL- 4-PYRAZOLEBORONIC ACID PINACOL ESTER;1-Benzyl-4-pyrazole boronic acid pinacol ester, 1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole,97%;1-benzyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyra;1H-Pyrazole, 1-(phenylMethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;1-(PhenylMethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, {[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}benzene;1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester 1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• CAS NO: 761446-45-1
• Molecular Formula: C₁₆H₂₁BN₂O₂
• Molecular Weight: 284.17
• EINECS: 2017-001-1
• Product Categories: API intermediates
• Mol File: 761446-45-1.mol

Chemical Properties

• Melting Point: 86-90 °C(lit.)
• Boiling Point: 427.932 °C at 760 mmHg
• Flash Point: 212.606 °C
• Appearance: off-white to light yellow crystal
• Density: 1.071 g/cm³
• Vapor Pressure: 3.93E-07mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 1.85±0.10(Predicted)
• Water Solubility: Insoluble
• CAS DataBase Reference: 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester(761446-45-1)
• EPA Substance Registry System: 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester(761446-45-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-23-22
• Safety Statements: 22-24/25-37/39-26-36/37/38
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 761446-45-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester is used as a model compound for studying the stability of boronate esters in different alcohols using the LCMS technique. This application helps researchers understand the reactivity and stability of boronate esters, which are important in the development of new synthetic methods and applications.
Used in Palladium-Catalyzed Reactions:
In the field of organic synthesis, 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester serves as a substrate in the study of palladium-catalyzed methylation of heteroaryl boronate esters using iodomethane. This research is crucial for the development of new cross-coupling reactions and the synthesis of complex organic molecules.
Used in the Preparation of Bromodifluoromethylthiolated Arenes:
1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester is also used as a substrate in the preparation of bromodifluoromethylthiolated arenes. These compounds are applicable in the radiosynthesis of [18F]ArylSCF3 compounds, which are valuable in the field of radiopharmaceuticals and molecular imaging, particularly for positron emission tomography (PET) applications.

InChI:InChI=1/C16H21BN2O2/c1-15(2)16(3,4)21-17(20-15)14-10-18-19(12-14)11-13-8-6-5-7-9-13/h5-10,12H,11H2,1-4H3

Upstream product

• 50877-41-3 1-benzyl-4-bromo-1H-pyrazole 
• 73183-34-3 bis(pinacol)diborane 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 50877-42-4 1-benzyl-4-iodo-1H-pyrazole 
• 100-39-0 benzyl bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 269410-08-4 pyrazole-4-boronic acid pinacol ester 

Downstream Products

• 1093307-32-4 5-(1-benzyl-1H-pyrazol-4-yl)-2-fluorobenzonitrile 
• 1309365-40-9 1-benzyl-4-(4-(trifluoromethyl)phenyl)-1H-pyrazole 
• 1604034-89-0 7-(1-benzyl-1H-pyrazol-4-yl)-2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine 
• 1093304-62-1 5-(1-benzyl-1H-pyrazol-4-yl)-1H-indazole 
• 145324-73-8 1-benzyl-4-methyl-1H-pyrazole 

Relevant articles and documents

Development of Inhibitors of SAICAR Synthetase (PurC) from Mycobacterium abscessus Using a Fragment-Based Approach

Mycobacterium abscessus (Mab) has emerged as a challenging threat to individuals with cystic fibrosis. Infections caused by this pathogen are often impossible to treat due to the intrinsic antibiotic resistance leading to lung malfunction and eventually death. Therefore, there is an urgent need to develop new drugs against novel targets in Mab to overcome drug resistance and subsequent treatment failure. In this study, SAICAR synthetase (PurC) from Mab was identified as a promising target for novel antibiotics. An in-house fragment library screen and a high-throughput X-ray crystallographic screen of diverse fragment libraries were explored to provide crucial starting points for fragment elaboration. A series of compounds developed from fragment growing and merging strategies, guided by crystallographic information and careful hit-to-lead optimization, have achieved potent nanomolar binding affinity against the enzyme. Some compounds also show a promising inhibitory effect against Mab and Mtb. This work utilizes a fragment-based design and demonstrates for the first time the potential to develop inhibitors against PurC from Mab.

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

THERAPEUTIC COMPOUNDS

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HETEROARYL COMPOUNDS AND PHARMACEUTICAL APPLICATIONS THEREOF

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Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies

A transition-metal-free method has been developed for the boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with a silylborane in the presence of an alkali-metal alkoxide. The base-mediated boryl substitution of organohalides with a silylborane was recently reported to provide the corresponding borylated products in good to high yields, and exhibit good functional group compatibility and high tolerance to steric hindrance. In this study, the scope of this transformation has been extended significantly to include a wide variety of functionalized aryl-, heteroaryl- and alkenyl halides. In particular, the boryl substitution of (E)- and (Z)-alkenyl halides proceeded smoothly to afford the corresponding alkenyl boronates in good to high yields with retention of the configuration using modified reaction conditions. The results of the mechanistic studies suggest that this boryl substitution proceeds via a carbanion-mediated mechanism.

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3-(PYRAZOLYL)-1H-PYRROLO[2,3-b]PYRIDINE DERIVATIVES AS KINASE INHIBITORS

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