Benzene, 1-bromo-4-(pentafluoroethoxy)-

Benzene, 1-bromo-4-(pentafluoroethoxy)- Property

Boiling point:

186℃

Density 

1.677

Flash point:

83℃

storage temp. 

2-8°C

Appearance

Colorless to light yellow Liquid

EPA Substance Registry System

Benzene, 1-bromo-4-(pentafluoroethoxy)- (56425-85-5)

Safety

HS Code 

2909309090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P310Immediately call a POISON CENTER or doctor/physician.

P330Rinse mouth.

P361Remove/Take off immediately all contaminated clothing.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

Benzene, 1-bromo-4-(pentafluoroethoxy)- Chemical Properties,Usage,Production

Application

4-Bromopentafluoroethoxybenzene is an organic intermediate that can be prepared in one step from (pentafluoroethyl)trimethylsilane and 4-bromophenol. Literature reports its potential use in preparing bile acid derivatives with FXR antagonistic function.

Synthesis

To a stirred solution of trifluoroethanol (10 g, 0.06 mol) in anhydrous dichloromethane (CH2Cl2, 100 mL) was added N,N-diisopropylethylamine (DIPEA; 29 mL, 0.16 mol) at room temperature and the reaction mixture was cooled to -78°C. At -78°C, trifluoromethanesulfonic anhydride (13.5 mL, 0.07 mol) to the reaction mixture. After stirring for 30 minutes, the reaction mixture was slowly warmed to -30°C and stirring was continued for 30 minutes. Upon completion of the reaction, the reaction was quenched with deionized water (200 mL) and extracted with dichloromethane (CH2Cl2, 2 x 300 mL). The organic layers were combined, washed sequentially with 1N hydrochloric acid (HCl) and deionized water, dried over anhydrous sodium sulfate (Na2SO4) and filtered. To a stirred N,N-dimethylformamide (DMF, 100 mL) solution of 4-bromophenol (4 g, 0.02 mol) and cesium carbonate (Cs2CO3; 15 g, 0.04 mol) was added the dichloromethane layer after the above treatment at room temperature. The mixture was stirred for 16 hours, during which time the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with deionized water and extracted with dichloromethane (CH2Cl2, 2 x 250 mL). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (SiO2, 60-120 mesh) to afford the target compound 1-bromo-4-(1,1,2,2,2-pentafluoroethoxy)benzene (3.5 g, 11.5 mmol, 50% yield) as a colorless liquid.1H NMR (200 MHz, CDCl3): δ 7.46-7.38 (m, 2H), 6.87- 6.79 (m, 2H), 4.45-4.32 (m, 2H).

References

[1] Patent: WO2013/110002, 2013, A1. Location in patent: Page/Page column 43-44