4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane
• CAS No.: 1381960-58-2
• Molecular Formula: C19H23BO2
• Molecular Weight: 294.201
• Hs Code.: 2931900090
• Mol file: 1381960-58-2.mol

Synonyms:4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane

Chemical Property of 4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane

Chemical Property:

• Boiling Point: 408.5±24.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 3.96120

Purity/Quality:

98% ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-[4-(4-methylphenyl)phenyl]-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane

There total 13 articles about 4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-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: 91.0%

para-bromotoluene (106-38-7) + trimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)stannane → 4,4,5,5-tetramethyl-2-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane (1381960-58-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃; for 12h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo402618r

Reference yield: 90.0%

4-methyl-4'-fluorobiphenyl (72093-43-7) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane (1381960-58-2)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; copper(l) iodide; cesium fluoride; tricyclohexylphosphine; In toluene; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jacs.5b10119

Reference yield: 33.0%

(4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane (1381960-58-2)

Guidance literature:

(4,4'-dimethyl-1,1'-biphenyl); With tert.-butylnitrite; N-hydroxyphthalimide; lithium bromide; In acetonitrile; at 80 ℃; for 24h; Inert atmosphere; Schlenk technique; Molecular sieve; Sealed tube;

bis(pinacol)diborane; With isonicotinate tert-butyl ester; at 110 ℃; for 21h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1002/anie.201901783

upstream raw materials:

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

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

para-bromotoluene

4-nitro-aniline

Downstream raw materials:

4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl

Refernces

• 1、 Shiozuka, Akira,Sekine, Kohei,Kuninobu, Yoichiro. "Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2". supporting information. p. 4774 - 4778. Retrieved 2021/06/28.
• 2、 Zhao, Xianghu,Wu, Mingsheng,Liu, Yisen,Cao, Song. "LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides". supporting information. p. 5564 - 5568. Retrieved 2018/09/12.