1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene

Base Information

• Chemical Name: 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene
• CAS No.: 269410-07-3
• Molecular Formula: C18H28B2O4
• Molecular Weight: 330.04
• Mol file: 269410-07-3.mol

Synonyms:1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene;2,2'-(1,2-Phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

Chemical Property of 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene

Chemical Property:

• Melting Point: 114.0 to 118.0 °C
• Boiling Point: 426.9±28.0 °C(Predicted)
• PSA: 36.92000
• Density: 1.03±0.1 g/cm3(Predicted)
• LogP: 2.28500
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,2''-(1,2-Phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane] ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene

There total 24 articles about 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene 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: 92.0%

ortho-difluorobenzene (367-11-3) + bis(pinacol)diborane (73183-34-3) → 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene (269410-07-3)

Guidance literature:

With chlorobis(tricyclohexylphosphine)copper(I); cesium fluoride; In toluene; at 80 ℃; for 24h;

DOI:10.1021/acscatal.7b01448

Reference yield: 80.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2-(2-bromophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (269410-06-2) → 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene (269410-07-3)

Guidance literature:

With magnesium; ethylene dibromide; In tetrahydrofuran; at 20 ℃; Reflux; Schlenk technique; Inert atmosphere;

DOI:10.1021/om500104w

Reference yield: 77.0%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + bis(pinacol)diborane (73183-34-3) → 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene (269410-07-3)

Guidance literature:

With potassium fluoride; Pt(dba)2; 18-crown-6 ether; 1-adamantyl isocyanide; In 1,2-dimethoxyethane; at 80 ℃; for 23h; Inert atmosphere;

DOI:10.1039/b919407j

upstream raw materials:

1-Bromo-2-iodobenzene

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

2,3-dibromobenzene

1,2-Diiodobenzene

Downstream raw materials:

1,2-di(thiophen-3-yl)benzene

2‐{[1,1'‐biphenyl]‐2‐yl}‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane

o-terphenyl

4'-acetyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl

Refernces

• 1、 Mahamudul Hassan, Mirja Md,Mondal, Biplab,Singh, Sukriti,Haldar, Chabush,Chaturvedi, Jagriti,Bisht, Ranjana,Sunoj, Raghavan B.,Chattopadhyay, Buddhadeb. "Ir-Catalyzed Ligand-Free Directed C-H Borylation of Arenes and Pharmaceuticals: Detailed Mechanistic Understanding". . p. 4360 - 4375. Retrieved 2022/03/16.
• 2、 Dong, Jie,Guo, Hui,Peng, Wei,Hu, Qiao-Sheng. "Room temperature Pd(0)/Ad3P-catalyzed coupling reactions of aryl chlorides with bis(pinacolato)diboron". supporting information. p. 760 - 763. Retrieved 2019/02/16.