1012085-50-5

Basic information

• Product Name: 3,5-Pridine diboronic acid pinacol ester
• Synonyms: 3,5-Pridine diboronic acid pinacol ester;3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS NO: 1012085-50-5
• Molecular Formula: C₁₇H₂₇B₂NO₄
• Molecular Weight: 331.02258
• Mol File: 1012085-50-5.mol

Chemical Properties

• Boiling Point: 445.6±30.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.21±0.24(Predicted)
• CAS DataBase Reference: 3,5-Pridine diboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pridine diboronic acid pinacol ester(1012085-50-5)
• EPA Substance Registry System: 3,5-Pridine diboronic acid pinacol ester(1012085-50-5)

Safety Data

• Hazardous Substances Data: 1012085-50-5(Hazardous Substances Data)

Usage

Uses

3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine

Upstream product

• 110-86-1 pyridine 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1197989-81-3 C₇₃H₄₉N₅ 

Relevant articles and documents

Enzyme-like Supramolecular Iridium Catalysis Enabling C?H Bond Borylation of Pyridines with meta-Selectivity

The use of secondary interactions between substrates and catalysts is a promising strategy to discover selective transition metal catalysts for atom-economy C?H bond functionalization. The most powerful catalysts are found via trial-and-error screening due to the low association constants between the substrate and the catalyst in which small stereo-electronic modifications within them can lead to very different reactivities. To circumvent these limitations and to increase the level of reactivity prediction in these important reactions, we report herein a supramolecular catalyst harnessing Zn???N interactions that binds to pyridine-like substrates as tight as it can be found in some enzymes. The distance and spatial geometry between the active site and the substrate binding site is ideal to target unprecedented meta-selective iridium-catalyzed C?H bond borylations with enzymatic Michaelis–Menten kinetics, besides unique substrate selectivity and dormant reactivity patterns.

Meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst

We report herein the iridium-catalyzed meta-selective C-H borylation of benzamides by using a newly designed 2,2′-bipyridine (bpy) ligand bearing an alkylaluminum biphenoxide moiety. We also demonstrate the iridium-catalyzed C3-selective C-H borylation of pyridine with a 1,10-phenanthroline (Phen) ligand bearing an alkylborane moiety. It is proposed that the Lewis acid-base interaction between the Lewis acid moiety and the aminocarbonyl group or the sp2-hybridized nitrogen atom accelerates the reaction and controls the site-selectivity.

para-Selective C?H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis

para-Selective C?H borylation of benzamides and pyridines has been achieved by cooperative iridium/aluminum catalysis. A combination of iridium catalysts commonly employed for arene C?H borylation and bulky aluminum-based Lewis acid catalysts provides an unprecedented strategy for controlling the regioselectivity of C?H borylation to give variously substituted (hetero)arylboronates, which are versatile synthetic intermediates for complex multi-substituted aromatic compounds.