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

Base Information

• Chemical Name: 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl
• CAS No.: 850264-92-5
• Molecular Formula: C24H32B2O4
• Molecular Weight: 406.138
• Mol file: 850264-92-5.mol

Synonyms:

Chemical Property of 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl

Chemical Property:

• Melting Point: 167 °C
• PSA: 36.92000
• LogP: 3.95200

Purity/Quality:

97% ^*data from raw suppliers

3,3'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl

There total 4 articles about 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl 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: 97.0%

3,3'-dibromobiphenyl (16400-51-4) + bis(pinacol)diborane (73183-34-3) → 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl (850264-92-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02379

Reference yield: 62.0%

trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane → 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl (850264-92-5)

Guidance literature:

With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); o-tetrachloroquinone; In chloroform; 1,2-dichloro-ethane; at 60 ℃; for 10h; Inert atmosphere;

DOI:10.1246/cl.170723

Reference yield:

(3-bromophenyl)boronic acid (89598-96-9) → 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl (850264-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,2-dimethoxyethane / 12 h / Reflux; Inert atmosphere

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 16 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium carbonate; In 1,2-dimethoxyethane; water; dimethyl sulfoxide;

upstream raw materials:

(3-bromophenyl)boronic acid

3,3'-dibromobiphenyl

bis(pinacol)diborane

1-Bromo-3-iodobenzene

Downstream raw materials:

C₂₄H₁₆Br₂