78782-17-9

Basic information

• Product Name: Bis[(pinacolato)boryl]Methane
• Synonyms: Bis[(pinacolato)boryl]Methane;2,2'-Methylenebis[4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;Bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)Methane;Bis[(pinacolato);4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane
• CAS NO: 78782-17-9
• Molecular Formula: C₁₃H₂₆B₂O₄
• Molecular Weight: 267.96514
• Product Categories: Boron Derivatives;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 78782-17-9.mol
• Article Data: 25

Chemical Properties

• Melting Point: 51.0 to 55.0 °C
• Boiling Point: 272.0±23.0 °C(Predicted)
• Flash Point: >110℃
• Appearance: /
• Density: 0.97±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Bis[(pinacolato)boryl]Methane(CAS DataBase Reference)
• NIST Chemistry Reference: Bis[(pinacolato)boryl]Methane(78782-17-9)
• EPA Substance Registry System: Bis[(pinacolato)boryl]Methane(78782-17-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 78782-17-9(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Low Melting Solid

Uses

Different sources of media describe the Uses of 78782-17-9 differently. You can refer to the following data:
1. Bis-boronate has been reported by Morken and coworkers to be a key building block in the synthesis of enantioenriched secondary boronate esters, which undergo facile Suzuki-Miyaura coupling with minimal erosion of enantiopurity.
2. An organoboronate derivative that is an inhibitor of matrix metallo-proteinase (MMP-2).

General Description

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Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 74-95-3 1,1-dibromomethane 
• 50-00-0 formaldehyd 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 17936-82-2 bis(dimethoxyboryl)methane 
• 186581-53-3 diazomethane 
• 201230-82-2 carbon monoxide 
• 75-09-2 dichloromethane 
• 15243-33-1 dodecacarbonyl-triangulo-triruthenium 
• 34557-54-5 methane 
• 110-82-7 cyclohexane 
• 287-92-3 Cyclopentane 
• 75-11-6 diiodomethane 
• 70557-99-2 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1535207-56-7 trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)(m-tolyl)methyl)silane 
• 1535207-57-8 ((3-chlorophenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)trimethylsilane 
• 1535207-59-0 trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)(o-tolyl)methyl)silane 
• 1535207-60-3 (biphenyl-2-yl(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)metyl)trimmethylsilane 
• 1535207-47-6 ((4-methoxyphenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)trimethylsilane 
• 1535207-50-1 trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)(p-tolyl)methyl)silane 
• 1535207-51-2 ((4-cyclohexylphenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)trimethylsilane 
• 1535207-52-3 ([1,1′-biphenyl]-4-yl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)trimethylsilane 
• 1535207-53-4 ((4-fluorophenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)trimethylsilane 
• 1535207-54-5 ((4-chlorophenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)trimethylsilane 
• 389-58-2 4H-cyclopenta[2,1-b;3,4-b']dithiophene 
• 1227056-27-0 2,2'-(2-cyclohexylethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 83947-58-4 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane 
• 169339-75-7 (E)-2-(hept-1'-en-1'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Catalytic borylation of methane

Despite steady progress in catalytic methods for the borylation of hydrocarbons, methane has not yet been subject to this transformation. Here we report the iridium-catalyzed borylation of methane using bis(pinacolborane) in cyclohexane solvent. Initially, trace amounts of borylated products were detected with phenanthroline-coordinated Ir complexes. A combination of experimental high-pressure and high-throughput screening, and computational mechanism discovery techniques helped to rationalize the foundation of the catalysis and identify improved phosphine-coordinated catalytic complexes. Optimized conditions of 150°C and 3500-kilopascal pressure led to yields as high as ～52%, turnover numbers of 100, and improved chemoselectivity for monoborylated versus diborylated methane.

An Olefinic 1,2-α-Boryl Migration Enables 1,2-Bis(boronic esters) via Radical-Polar Crossover Reaction

A radical-induced 1,2-α-boryl migration through radical polar crossover reactions has been described. In this work, in situ formed vinyldiboron “ate” complexes from alkenyl Grignard reagent and diborylalkanes react with commercial radical precursors under light initiation. This three-component process enables diborylation of alkene. This protocol features high atom economy, a broad substrate scope as well as good functional group toleration with mild conditions.

Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A

Aspochalasins are leucine-derived cytochalasins. Their complexity is associated with a high degree of biosynthetic oxidation, herein inspiring a two-phase strategy in total synthesis. We thus describe the synthesis of a putative biomimetic tetracyclic int