5-FLUOROBENZENE-1,3-DIOL Chemical Properties

Melting point:

136.0 to 140.0 °C

Boiling point:

237.9±10.0 °C(Predicted)

Density 

1.415±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Practically insoluble in water

form 

powder to crystal

pka

8.45±0.10(Predicted)

color 

White to Light yellow to Light orange

Safety Information

HS Code 

2908190090

5-FLUOROBENZENE-1,3-DIOL Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-fluororesorcinol from 1,3-dimethoxy-5-fluorobenzene: 1,3-dimethoxy-5-fluorobenzene (10 g, 64 mmol) was dissolved in anhydrous dichloromethane (40 mL) and the solution was cooled to -30 °C. A solution of BBr3 (35.93 mL, 384 mmol) in 60 mL of dichloromethane was added slowly and dropwise to the cooled solution over 30 minutes. After the dropwise addition, the reaction mixture was slowly warmed to 25 °C and stirred continuously for 12 hours. The reaction process was monitored by thin layer chromatography (TLC) using 30% ethyl acetate and petroleum ether as elution solvents. Upon completion of the reaction, the mixture was cooled to 0 °C and quenched by the slow addition of water, followed by stirring at 25 °C for 30 min. The reaction mixture was extracted with dichloromethane (3 x 100 mL), and the combined organic layers were washed with sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated to give 5-fluororesorcinol (2) as a light brown solid. Yield: 8 g (97%).

References

[1] Patent: WO2013/90921, 2013, A1. Location in patent: Paragraph 00154
[2] Patent: WO2014/153000, 2014, A1. Location in patent: Paragraph 0321
[3] Patent: US2016/60260, 2016, A1. Location in patent: Paragraph 0237
[4] Journal of Organic Chemistry, 1997, vol. 62, # 19, p. 6469 - 6475
[5] Journal of Materials Chemistry, 2002, vol. 12, # 5, p. 1316 - 1324