Bis[(pinacolato)boryl]methane

Base Information

• Chemical Name: Bis[(pinacolato)boryl]methane
• CAS No.: 78782-17-9
• Molecular Formula: C13H26B2O4
• Molecular Weight: 267.969
• Hs Code.: 2931900090
• European Community (EC) Number: 810-358-7
• DSSTox Substance ID: DTXSID80462021
• Nikkaji Number: J1.364.450K
• Wikidata: Q82286484
• Mol file: 78782-17-9.mol

Synonyms:Bis[(pinacolato)boryl]methane;78782-17-9;Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methane;4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane;Bis((pinacolato)boryl)methane;MFCD27977747;2,2'-Methylenebis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane);2,2'-Methylenebis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane];Methylenedi(boronic Acid Pinacol Ester);SCHEMBL10001281;AMY1128;DTXSID80462021;1,3,2-Dioxaborolane, 2,2'-methylenebis[4,4,5,5-tetramethyl-;AKOS027324523;DS-11521;SY040252;B4103;CS-0153823;FT-0663384;EN300-214736;H10252;A914795;4,4,5,5-tetramethyl-2-[(tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane

Chemical Property of Bis[(pinacolato)boryl]methane

Chemical Property:

• Melting Point: 51.0 to 55.0 °C
• Boiling Point: 272.0±23.0 °C(Predicted)
• Flash Point: >110℃
• PSA: 36.92000
• Density: 0.97±0.1 g/cm3(Predicted)
• LogP: 2.71000
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 268.2017196
• Heavy Atom Count: 19
• Complexity: 300

Purity/Quality:

97% ^*data from raw suppliers

Bis[(pinacolato)boryl]methane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CB2OC(C(O2)(C)C)(C)C
• Uses: 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. An organoboronate derivative that is an inhibitor of matrix metallo-proteinase (MMP-2).

Technology Process of Bis[(pinacolato)boryl]methane

There total 12 articles about Bis[(pinacolato)boryl]methane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

bis(pinacol)diborane (73183-34-3) + 1,1-dibromomethane (74-95-3) → 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9)

Guidance literature:

With copper(l) iodide; lithium methanolate; In N,N-dimethyl-formamide; at 40 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/ol503111h

Reference yield: 83.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9)

Guidance literature:

tetrakis(triphenylphosphine)platinum; In diethyl ether; to Pt(PPh3)4 and bis(pinacolato)diborane(4) in Et2O was added slowly at 0°C diazomethane in Et2O, after 2 h soln. was warmed to room temp. and stirred overnight; solvent was removed under vac., residue was extd. with pentane, solvent was removed under vac., residue was chromed. on silica (10 % Et2O - petroleum ether); elem. anal.;

DOI:10.1021/om010282r

Reference yield: 80.0%

diiodomethane (75-11-6) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9)

Guidance literature:

diiodomethane; With isopropylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 2.5h; Inert atmosphere;

bis(pinacol)diborane; In tetrahydrofuran; at -78 - 55 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jacs.5b03477

upstream raw materials:

diazomethane

bis(pinacol)diborane

2,3-dimethyl-2,3-butane diol

bis(dimethoxyboryl)methane

Downstream raw materials:

2-(2-fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(3-methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(3-fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane