4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane
• CAS No.: 1161009-89-7
• Molecular Formula: C31H27BO2
• Molecular Weight: 442.365
• Mol file: 1161009-89-7.mol

Synonyms:4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane;9,9'-Spirobi[9H-fluoren]-4-ylboronic acid pinacol ester

Chemical Property of 4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane

Chemical Property:

• Melting Point: 216.0 to 220.0 °C
• Boiling Point: 585.6±29.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 6.32930
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

4-(9,9''-Spirobifluorenyl)pinacolboronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 4-(9,9''-Spirobifluorenyl)pinacolboronate acts as a reagent in the synthesis of new blue dual-core OIED emitters using Suzuki coupling reactions with (spirobifluorenyl)pinacolboronate or (borophenyl)carbazole.

Technology Process of 4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane

There total 14 articles about 4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-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: 96.0%

4-bromo-9,9’-spirobi[9H-fluorene] (1161009-88-6) + bis(pinacol)diborane (73183-34-3) → 2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1161009-89-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; In toluene; for 16h; Reflux;

Reference yield: 90.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4-bromo-9,9’-spirobi[9H-fluorene] (1161009-88-6) → 2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1161009-89-7)

Guidance literature:

4-bromo-9,9’-spirobi[9H-fluorene]; With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at -78 - 20 ℃; for 12h;

Reference yield: 77.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4-bromo-9H-fluorene-9-one (4269-17-4) → 2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1161009-89-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201813604

upstream raw materials:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-bromo-9,9’-spirobi[9H-fluorene]

bis(pinacol)diborane

2-Bromobiphenyl

Downstream raw materials:

C₃₁H₁₈BrCl

Refernces

• 1、 -. "Organometallic complex and organic elcetroluminescent device including the same". Paragraph 0192-0194. . Retrieved 2021/08/10.
• 2、 -. "COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF". Paragraph 0225; 0517; 0622-0625; 0701. . Retrieved 2020/06/02.