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

Base Information

• Chemical Name: 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 68716-49-4
• Molecular Formula: C12H16BBrO2
• Molecular Weight: 282.973
• Hs Code.: 2934999090
• European Community (EC) Number: 801-957-4
• DSSTox Substance ID: DTXSID30444493
• Nikkaji Number: J1.423.512D
• Wikidata: Q72449251
• Mol file: 68716-49-4.mol

Synonyms:68716-49-4;2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Bromophenylboronic acid pinacol ester;4-Bromophenylboronic acid, pinacol ester;1,3,2-Dioxaborolane, 2-(4-bromophenyl)-4,4,5,5-tetramethyl-;2-(4-bromo-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;MFCD11110553;(4-BROMOPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL171682;DTXSID30444493;AZCNDGAXOZWQPV-UHFFFAOYSA-N;AKOS016004712;4-Bromophenylboronic acid,pinacol ester;AS-2516;tetra-methylethylene p-bromophenylboronate;SY037980;B4771;CS-0036048;FT-0739764;EN300-316477;Z2044796873;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene;1-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;4-bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

Chemical Property of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 69.0 to 73.0 °C
• Boiling Point: 324.147oC at 760 mmHg
• Flash Point: 149.839oC
• PSA: 18.46000
• Density: 1.297g/cm3
• LogP: 2.74830
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 282.04267
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

98% ^*data from raw suppliers

4-BroMophenylboronic acid pinacol ester ^*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)C2=CC=C(C=C2)Br

Technology Process of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 56 articles about 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 100.0%

bromobenzene (108-86-1,52753-63-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → p-bromophenylboronic acid pinacol ester (68716-49-4)

Guidance literature:

[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF₃CO₂; at 40 ℃; for 10h;

DOI:10.1016/j.jorganchem.2006.08.099

Reference yield: 99.7%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-Bromophenylboronic acid (5467-74-3) → p-bromophenylboronic acid pinacol ester (68716-49-4)

Guidance literature:

In acetonitrile; at 20 ℃; for 1.5h;

Reference yield: 95.0%

4-bromobenzenediazonium tetrafluoroborate (673-40-5) + bis(pinacol)diborane (73183-34-3) → p-bromophenylboronic acid pinacol ester (68716-49-4)

Guidance literature:

With 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; palladium diacetate; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1021/ol035857q

upstream raw materials:

4-bromobenzenediazonium tetrafluoroborate

bis(pinacol)diborane

1,4-bromoiodobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

benzene-1,4-diboronic acid bispinacol ester

phenyl-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

dimethyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phosphonate

2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie. "Cross-Coupling through Ag(I)/Ag(III) Redox Manifold". supporting information. p. 15396 - 15405. Retrieved 2021/10/12.
• 2、 Cui, Enxin,Guo, Lirong,Li, Haibin,Qiao, Dan,Tung, Chen-Ho,Wang, Yifeng. "Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation". . p. 255 - 263. Retrieved 2021/09/06.