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

Melting point:

216.0 to 220.0 °C

Boiling point:

585.6±29.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

color 

White to Almost white

Safety Information

HS Code 

2931.90.6000

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

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.

Synthesis

General procedure for the synthesis of 2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes from 4-bromo-9,9'-spirobi(fluorene) and bipinacolate: 1. 60 g (152 mmol) of 4-bromo-9,9'-spirobifluorene, 47.2 g (182.1 mmol) of pinacol ester of bisboronic acid, 3.72 g (4.55 mmol) of 1,1'-bis(diphenylphosphino)-ferrocene-palladium(II) dichloromethane complex and 44.7 g (455 mmol) of potassium acetate were dissolved in 600 ml of toluene. 2. The reaction mixture was heated under reflux conditions for 16 hours. 3. After completion of the reaction, cool to room temperature, add 200 ml of water and continue stirring for 30 minutes. 4. Separate the organic phase and filter through a short diatomaceous earth bed. 5. The solvent was removed by pressure reducing distillation. 6. The residue was purified by multiple recrystallization through a heptane/toluene solvent mixture. 7. 67.1 g of product was obtained in 96% yield.

References

[1] Patent: WO2016/78738, 2016, A1. Location in patent: Page/Page column 66
[2] Patent: WO2012/56919, 2012, A1. Location in patent: Page/Page column 35; 37
[3] Patent: CN108658932, 2018, A. Location in patent: Paragraph 0066; 0067; 0068

4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane(1161009-89-7)Related Product Information

• 9,9'-spirobi[fluorene]-2,2'-diyldiboronic acid pinacol ester
• 1,3,2-DIOXABOROLANE, 2-(9,9-DIMETHYL-9H-FLUOREN-2-YL)-4,4,5,5-TETRAMETHYL
• 9,9-Diphenylfluorene-2-Boronic acid pinacol ester
• 9,9'-spirobi[fluorene]-2,2'-diyldiboronic acid
• (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE)
• 9,9-DiMethylfluorene-3-boronic acid pinacol ester
• 9,9-Spirodifluorene-2-Boronic acid pinacol ester
• 4 - boric acid pinacol ester - 9, 9 - dimethyl fluorene
• 9,9-Spirodifluorene-3-Boronic acid pinacol ester
• 9,9-diphenyl-9H-fluoreN-4-ylboronicacid
• 4-Pinacol ester-9,9-dipehnylfluorene
• 1,3,2-DIOXABOROLANE, 2,2'-(9,9-DIMETHYL-9H-FLUORENE-2,7-DIYL)BIS[4,4,5,5-TETRAMETHYL]
• 9,9-diphenyl-fluoren-3-boronic acid pinacol ester