4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile

Base Information

• Chemical Name: 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile
• CAS No.: 406482-72-2
• Molecular Formula: C19H20BNO2
• Molecular Weight: 305.184
• Hs Code.: 2934999090
• European Community (EC) Number: 878-924-6
• DSSTox Substance ID: DTXSID50473866
• Wikidata: Q82303533
• Mol file: 406482-72-2.mol

Synonyms:406482-72-2;4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile;4-(4-Cyanophenyl)phenylboronic acid, pinacol ester;4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carbonitrile;4-(4-Cyanophenyl)phenylboronic acid pinacol ester;4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzonitrile;MFCD17015781;4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-4-carbonitrile;C19H20BNO2;SCHEMBL15301292;DTXSID50473866;AKOS022184052;BS-17224;SY283478;CS-0160977;D70739;A930640;4 inverted exclamation mark -Cyanobiphenyl-4-boronic Acid Pinacol Ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1-biphenyl]-4-carbonitrile

Chemical Property of 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile

Chemical Property:

• Boiling Point: 450.8±38.0 °C(Predicted)
• PSA: 42.25000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 3.52448
• Storage Temp.: Room temperature.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 305.1587090
• Heavy Atom Count: 23
• Complexity: 449

Purity/Quality:

99% ^*data from raw suppliers

4-(4-Cyanophenyl)phenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C3=CC=C(C=C3)C#N

Technology Process of 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile

There total 14 articles about 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile 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:

2-(4-bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione + 4-cyanophenylboronic acid pinacol ester (171364-82-2) → 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-carbonitrile (406482-72-2)

Guidance literature:

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; water; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c5ob00078e

Reference yield:

1.4-dibromobenzene (106-37-6) → 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-carbonitrile (406482-72-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran; hexane / 0 h / -20 °C / Flow reactor

1.2: 0 h / -20 °C / Flow reactor

2.1: sec.-butyllithium / tetrahydrofuran; hexane / -70 °C / Flow reactor

2.2: 0.03 h / -70 °C / Flow reactor

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; hexane / 2 h / 20 °C / Schlenk technique; Inert atmosphere

3.2: 0.5 h / 25 °C / Schlenk technique; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sec.-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1021/jacs.0c06370

Reference yield:

4-iodobenzonitrile (3058-39-7) + tributyl(4-(3,3,4,4-tetramethyl-1l3,2,5-boradioxolan-1-yl)phenyl)stannane → 4-tri-n-butylstannyl-4'-cyanobiphenyl + 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-carbonitrile (406482-72-2)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; In ethanol; water; at 50 ℃; for 4h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jacs.0c06370

upstream raw materials:

4-cyanophenylboronic acid pinacol ester

4-Bromophenylboronic acid

4-iodobenzonitrile

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

4-Cyano-4'-hydroxybiphenyl

Refernces

• 1、 -. "Electron transport material, organic electro-luminescent device and display device". . . Retrieved 2021/01/24.
• 2、 Nagaki, Aiichiro,Ashikari, Yosuke,Kawaguchi, Tomoko,Mandai, Kyoko,Aizawa, Yoko. "A synthetic approach to dimetalated arenes using flow microreactors and the switchable application to chemoselective cross-coupling reactions". supporting information. p. 17039 - 17047. Retrieved 2020/11/10.