847818-79-5

Basic information

• Product Name: 1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE
• Synonyms: 1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE;1,3-Dimethylpyrazole-5-boronic acid pinacol ester;1,3-Dimethylpyrazole-5-bo...;1,3-Dimethyl-1H-pyrazole-5-boronic acid, pinacol ester;1H-Pyrazole, 1,3-diMethyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;1,3-DiMethylpyrazole-5-boronic Acid Pinacol Ester, 95+%;1,3-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• CAS NO: 847818-79-5
• Molecular Formula: C₁₁H₁₉BN₂O₂
• Molecular Weight: 222.09
• Mol File: 847818-79-5.mol

Chemical Properties

• Boiling Point: 326.7°C at 760 mmHg
• Flash Point: 151.4°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 0.000403mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: Refrigerated.
• PKA: 2.41±0.10(Predicted)
• CAS DataBase Reference: 1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE(847818-79-5)
• EPA Substance Registry System: 1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE(847818-79-5)

Safety Data

• Hazardous Substances Data: 847818-79-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique boron-containing group and pyrazole structure contribute to the creation of novel drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE is utilized as a key component in the synthesis of innovative agrochemicals. Its properties allow for the development of new pesticides or herbicides with improved efficacy and selectivity.
Used in Materials Science:
1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE is employed as a building block for the design of advanced materials with specific properties. Its incorporation into materials can lead to new applications in areas such as catalysis, sensors, or energy storage.
Used in Organic Electronics and Optoelectronics:
1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE is used as a functional material in the development of organic electronics and optoelectronic devices. The presence of a boron-containing group enhances its potential for use in these high-tech applications, contributing to the advancement of flexible electronics, light-emitting diodes (LEDs), and photovoltaic cells.
Further research and exploration of 1,3-DIMETHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE could unlock new possibilities and drive scientific advancements in multiple disciplines.

InChI:InChI=1/C11H19BN2O2/c1-8-7-9(14(6)13-8)12-15-10(2,3)11(4,5)16-12/h7H,1-6H3

Upstream product

• 694-48-4 1,3-dimethyl-1H-pyrazole 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 847818-68-2 (1,3-dimethyl-1H-pyrazol-5-yl)boronic acid 

Relevant articles and documents

Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand

The steric effects of substituents on five-membered rings are less pronounced than those on six-membered rings because of the difference in bond angles. Thus, the regioselectivities of reactions of five-membered heteroarenes that occur with selectivities dictated by steric effects, such as the borylation of C?H bonds, have been poor in many cases. We report that the silylation of five-membered-ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of [Ir(cod)(OMe)]2 (cod=1,5-cyclooctadiene) and a phenanthroline ligand or a new pyridyl-imidazoline ligand that further increases the regioselectivity. The silylation reactions with these catalysts produce high yields of heteroarylsilanes from functionalization at the most sterically accessible C?H bonds of these rings under conditions that the borylation of C?H bonds with previously reported catalysts formed mixtures of products or products that are unstable. The heteroarylsilane products undergo cross-coupling reactions and substitution reactions with ipso selectivity to generate heteroarenes that bear halogen, aryl, and perfluoroalkyl substituents.

Synthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids

Starting from 1H-pyrazol, a wide number of 1-alkyl-1H-pyrazol-4-yl and 1-alkyl-1H-pyrazol-5-ylboronic acids and their pinacol esters were synthesized and characterized. The key step in the described methodology is the regioselective lithiation of the pyrazole ring. The synthesized pinacolates are stable under prolonged storage and can be used as convenient reagents in organic synthesis.