1,3-phenyldiboronic acid, bis(pinacol) ester

Base Information

• Chemical Name: 1,3-phenyldiboronic acid, bis(pinacol) ester
• CAS No.: 196212-27-8
• Molecular Formula: C18H28B2O4
• Molecular Weight: 330.04
• Hs Code.: 2934999090
• Mol file: 196212-27-8.mol

Synonyms:4,4,5,5-Tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane;1,3-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;

Chemical Property of 1,3-phenyldiboronic acid, bis(pinacol) ester

Chemical Property:

• Vapor Pressure: 3.15E-07mmHg at 25°C
• Melting Point: 133.0 to 137.0 °C
• Refractive Index: 1.49
• Boiling Point: 430.902 °C at 760 mmHg
• Flash Point: 214.402 °C
• PSA: 36.92000
• Density: 1.036 g/cm³
• LogP: 2.28500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol

Purity/Quality:

99% ^*data from raw suppliers

1,3-bis(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3-phenyldiboronic acid, bis(pinacol) ester

There total 23 articles about 1,3-phenyldiboronic acid, bis(pinacol) ester 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%

1,3-dibromobenzene (108-36-1) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane (196212-27-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In N,N-dimethyl-formamide; at 90 ℃; for 48h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.9b03202

Reference yield: 84.0%

1,3-Difluorobenzene (372-18-9) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane (196212-27-8)

Guidance literature:

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

DOI:10.1021/acscatal.7b01448

Reference yield: 80.0%

1-bromo-3-chlorobenzene (108-37-2) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane (196212-27-8)

Guidance literature:

With pyridine-4-carbonitrile; potassium phosphate; sodium oxalate; 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile; In acetonitrile; at 20 ℃; for 24h; Irradiation; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c05994

upstream raw materials:

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

benzene

1,3-dibromobenzene

bis(pinacol)diborane

Downstream raw materials:

m-quinquephenyl

Refernces

• 1、 Büldt, Laura A.,Guo, Xingwei,Prescimone, Alessandro,Wenger, Oliver S.. "A Molybdenum(0) Isocyanide Analogue of Ru(2,2′-Bipyridine)32+: A Strong Reductant for Photoredox Catalysis". . p. 11247 - 11250. Retrieved 2016.
• 2、 Sun, Zhe,Mio, Tatsuru,Ikemoto, Koki,Sato, Sota,Isobe, Hiroyuki. "Synthesis, Structures, and Assembly of Geodesic Phenine Frameworks with Isoreticular Networks of [ n]Cyclo- para-phenylenes". . p. 3500 - 3507. Retrieved 2019.
• 3、 Full, Julian,Panchal, Santosh P.,G?tz, Julian,Krause, Ana-Maria,Nowak-Król, Agnieszka. "Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices". supporting information. p. 4350 - 4357. Retrieved 2021/01/29.
• 4、 K?nig, Burkhard,Wang, Hua,Wang, Shun. "Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation". supporting information. p. 1653 - 1665. Retrieved 2021/06/17.