1,3,2-DIOXABOROLANE, 2-(9,9-DIMETHYL-9H-FLUOREN-2-YL)-4,4,5,5-TETRAMETHYL Chemical Properties

Melting point:

134.0 to 138.0 °C

Boiling point:

443.1±24.0 °C(Predicted)

Density 

1.09±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

InChI

InChI=1S/C21H25BO2/c1-19(2)17-10-8-7-9-15(17)16-12-11-14(13-18(16)19)22-23-20(3,4)21(5,6)24-22/h7-13H,1-6H3

InChIKey

DAZFRJAIIUPRQZ-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1C1C=CC2C3=C(C(C)(C)C=2C=1)C=CC=C3

Safety Information

WGK Germany 

3

HS Code 

2931900090

1,3,2-DIOXABOROLANE, 2-(9,9-DIMETHYL-9H-FLUOREN-2-YL)-4,4,5,5-TETRAMETHYL Usage And Synthesis

Uses

9,9-Dimethylfluorene-2-boronic acid pinacol ester can be used in the synthesis of 1,2-diphenylindolizine derivatives for potential usage in organic light emitting diodes (OLEDs). It can also be used in the synthesis of pyrene-fluorene based chromophores for applications in photocatalysis and organic electronic devices.

Synthesis

Under nitrogen protection, 2-bromo-9,9-dimethylfluorene (100 g, 366 mmol, purchased from Sigma Aldrich Co., Ltd.) was dissolved in dimethylformamide (DMF, 1.1 L). Subsequently, bis(pinacolato)diboron (112 g, 439 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (2.99 g, 3.66 mmol) and potassium acetate (108 g, 1,098 mmol) were added to the solution. The reaction mixture was heated to 150 °C and refluxed for 5 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered and dried in a vacuum oven. The resulting residue was separated and purified by fast column chromatography to afford the target product fluorene-2-boronic acid katanol ester (102 g, 87% yield). High resolution mass spectrometry (HRMS, 70 eV, EI+): m/z calculated value of C21H25BO2[M]+ was 320.1948, measured value was 320. elemental analysis results: C, 79%; H, 8%.

References

[1] Patent: US2017/373255, 2017, A1. Location in patent: Paragraph 0164; 0165; 0166; 0167
[2] Patent: KR2017/88601, 2017, A. Location in patent: Paragraph 0160-0165
[3] Patent: WO2013/180376, 2013, A1. Location in patent: Paragraph 138; 139; 140
[4] Patent: US9825230, 2017, B2. Location in patent: Page/Page column 34

1,3,2-DIOXABOROLANE, 2-(9,9-DIMETHYL-9H-FLUOREN-2-YL)-4,4,5,5-TETRAMETHYL(569343-09-5)Related Product Information

• 1,3,2-DIOXABOROLANE, 2,2'-(9,9-DIMETHYL-9H-FLUORENE-2,7-DIYL)BIS[4,4,5,5-TETRAMETHYL]
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• 1,3,2-DIOXABOROLANE, 2-(9,9-DIMETHYL-9H-FLUOREN-2-YL)-4,4,5,5-TETRAMETHYL
• 3,4-Dimethylphenylboronic acid
• 3-ISOPROPYLBENZENEBORONIC ACID ETHYLENE GLYCOL ESTER
• 3-BENZYLPHENYLBORONIC ACID PINACOL ESTER
• 4-BIPHENYLBORONIC ACID, PINACOL ESTER
• M-T-BUTYLPHENYLBORONIC ACID