Description
2-Bromo-9-fluorenone is a brominated derivative of 9-Fluorenone which is used in the preparation of antimalarial drugs. It is used as organic intermediates functional materials. It is mainly used as best liquid crystal material. It is used as an OLED intermediate. the maximum and minimum solubility of 2-bromo-9-fluorenone was 0.0526 (mole fraction) in 1,4-dioxane at 323.15 K and 0.0002 (mole fraction) in methanol at 278.15 K, respectively, and the solubility increased with the increase in temperature in all solvents[1].
Chemical Properties
yellow powder
Uses
2-Bromo-9-fluorenone, a functional material as an organic intermediate. It is the best liquid crystal material and is used as an intermediate for OLED.
Application
2-Bromo-9-fluorenone was used:
as end-capping agent for poly(9,9-dialkylfluorene-2,7-diyl) derivatives
in synthesis of 2-bromo-9-hydroxy-9-(2-biphenyl)fluorene
in preparation of spirobifluorene ligands
in synthesis of altitudinal molecular motors which contain functional groups in their rotor part
in synthesis of FB
Synthesis
The synthesis of 2-Bromo-9-fluorenone is as follows：the 9-fluorenone (10mmol), the phase transfer catalyst (1.5mmol fourteen alkyl trimethyl ammonium chloride) and brominated aqueous ammonium solution (30 wt %, 25mmol ammonium bromide) mixing and heating system temperature to 75 °C, in 1h is divided into three time 11mmol potassium bromate, to three times the weight ratio of 1:3:1, to maintain the system temperature to continue reaction 3h, wherein the 9-fluorenone, ammonium bromide, the molar ratio of potassium bromate 1 : 2.5: 1.1 ; 9-fluorenone, and fourteen alkyl trimethyl ammonium chloride (phase-transfer catalyst) molar ratio of 1 : 0.15; 2) after the reaction, to room temperature, by adding 20% aqueous solution of sodium sulfite ( eliminates the bromine fluid ), is filtered, the filter cake washing water And dried to obtain yellow solid of 2-Bromo-9-fluorenone, the yield is 99.2%.
Solubility in organics
2-Bromo-9-fluorenone was 0.0526 (mole fraction) in 1,4-dioxane at 323.15 K and 0.0002 (mole fraction) in methanol at 278.15 K, respectively, and the solubility increased with the increase in temperature in all solvents.
References
[1] Peng Y, et al. Determination and Analysis of Solubility of 2-Bromo-9-fluorenone in 10 Different Organic Solvents and Three Binary Solvent Mixtures at Different Temperatures (T = 278.15–323.15 K). Journal of Chemical & Engineering Data, 2022; 67: 2662–2674.
