9,9-Didecyl-2,7-dibromofluorene Chemical Properties

Melting point:

38.0 to 42.0 °C

Boiling point:

610.3±48.0 °C(Predicted)

Density 

1.166

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Tetrahydrofuran

form 

powder to crystal

color 

White to Light yellow to Light orange

Safety Information

HS Code 

2903.99.8001

9,9-Didecyl-2,7-dibromofluorene Usage And Synthesis

Uses

9,9-Didecyl-2,7-dibromofluorene (CAS# 175922-78-8) is a useful building block and has been used in the preparation of heat-resistant, fluorescent polyfluorene, as well as in the preparation of conducting polymer for use in solar cells.

Synthesis

Example 1 Synthesis of 2,7-dibromo-9,9-didecylfluorene: 2,7-dibromofluorene (64.8 g, 0.20 mol), potassium iodide (3.0 g, 0.018 mol), finely powdered potassium hydroxide (56.0 g, 1 mol) and dimethyl sulfoxide (150 mL) were added to a three-necked, round-bottomed flask under nitrogen protection with mechanical stirring. The flask was cooled in an ice-water bath and decyl bromide (90 mL, 95.94 g, 0.434 mol) was subsequently added in four batches. Note that the internal temperature rises significantly during the addition process. Once the last addition was completed, the reaction mixture was continued to be stirred at room temperature for 4 hours. At the end of the reaction, the reaction was quenched by the addition of water (200 mL) and the solid product was collected by filtration. The resulting solid was dried in a desiccator containing phosphorus pentoxide for 16 hours. The crude product was purified by ethanol recrystallization to afford 2,7-dibromo-9,9-didecylfluorene as white crystals (melting point 40-41 °C) in 92.7% yield. Mass spectrometry analysis showed molecular ion peaks m/z of 602, 604, 606 (M+), fragment ion peaks m/z of 461, 463, 465 (M-C10H21), and 382, 384 (461-Br). Elemental analysis results: calculated values for C33H48Br2: C, 65.56%; H, 8.00%; Br, 26.44%. Measured values: C, 64.99%; H, 8.21%; Br, 27.25%.

References

[1] Patent: US6730793, 2004, B1. Location in patent: Page column 3
[2] Polymer, 2014, vol. 55, # 26, p. 6696 - 6707
[3] Patent: US2018/273524, 2018, A1. Location in patent: Paragraph 0041
[4] Molecular Crystals and Liquid Crystals, 2013, vol. 578, # 1, p. 26 - 32
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 17, p. 2774 - 2784