3-DroMo-9,9'-spirobifluorene Chemical Properties

Boiling point:

508.6±29.0 °C(Predicted)

Density 

1.52±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

InChI

InChI=1S/C25H15Br/c26-16-13-14-24-20(15-16)19-9-3-6-12-23(19)25(24)21-10-4-1-7-17(21)18-8-2-5-11-22(18)25/h1-15H

InChIKey

UIUSRIQSFHZPSQ-UHFFFAOYSA-N

SMILES

C12(C3=C(C=CC=C3)C3=C1C=CC=C3)C1=C(C=CC=C1)C1=C2C=CC(Br)=C1

3-DroMo-9,9'-spirobifluorene Usage And Synthesis

Chemical Properties

off-white powder

Synthesis

The synthesis of the compound was carried out in two steps. Step 1: 2-Bromobiphenyl (1.05 eq., 4.0 g, 16.5 mmol) was dissolved in anhydrous ether (102 mL), and after the solution was cooled to -60 °C, n-butyllithium (n-BuLi, 1.16 eq.) was added slowly and dropwise. After maintaining this temperature for 10 minutes, a white precipitate was observed to be generated and the reaction mixture was subsequently warmed to room temperature to dissolve the precipitate. Next, 3-bromo-9H-fluoren-9-one was added and the reaction mixture was stirred at 45 °C overnight. After completion of the reaction, the reaction was quenched by adding 5% aqueous ammonium chloride solution (260 mL) and the organic phase was extracted with ether to give the alcohol intermediate (7.0 g). Step 2: The above alcohol intermediate was dissolved in acetic acid (141 mL) and hydrolyzed by adding 10% HCl/dioxane solution (78 mL, 10 mol%, 20 eq.). After evaporation to remove the solvent, the residual solid was purified by normal-phase fast chromatography to finally obtain 3-bromo-9,9'-spirobifluorene (5.86 g, 94% yield).

References

[1] Patent: EP2574608, 2013, A1. Location in patent: Paragraph 0088; 0089; 0090; 0091
[2] Patent: US9076971, 2015, B2. Location in patent: Page/Page column 9-10

3-DroMo-9,9'-spirobifluorene(1361227-58-8)Related Product Information

• 3-BROMO-4-CHLOROBENZONITRILE
• (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE)
• 3-BroMo-9,9-diphenyl-9H-fluorene
• 2,7-Dibromo-9,9'-spiro-bifluorene
• 1,3,2-DIOXABOROLANE, 2,2'-(9,9-DIMETHYL-9H-FLUORENE-2,7-DIYL)BIS[4,4,5,5-TETRAMETHYL]
• 4-BroMo-9,9-diphenyl fluorene
• 2-Bromo-9,9'-spirobi[9H-fluorene]
• 4-bromo-9,9'-Spirobi[9H-fluorene
• 3-Bromo-9,9-dimethylfluorene