2-CHLORO-5-FLUOROANISOLE Chemical Properties

Boiling point:

195 °C / 757mmHg

Density 

1.28

refractive index 

1.519

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

color 

Clear colorless

CAS DataBase Reference

450-89-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38-36/38

Safety Statements 

16-26-36-37/39-35-28-15-3/9

RIDADR 

1993

Hazard Note 

Irritant

HS Code 

29093090

2-CHLORO-5-FLUOROANISOLE Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS LIQUID

Synthesis

To a solution of 2-chloro-5-fluorophenol (959 mg, 6.54 mmol) in N,N-dimethylformamide (DMF, 15 mL) was added 60% sodium hydride (NaH, 496 mg, 12.4 mmol) in batches at 0 °C. After the hydrogen bubbling stopped, iodomethane (0.43 mL, 6.91 mmol) was added and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was slowly poured into a beaker containing water and crushed ice, alkalized with saturated aqueous sodium bicarbonate (NaHCO3) and extracted with dichloromethane (DCM). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using hexane:ethyl acetate (9:1) as eluent to afford 1-chloro-4-fluoro-2-methoxybenzene (600 mg) as a colorless oil. High performance liquid chromatography (HPLC, 254 nm) retention time (Rt): 6.15 min. 1H nuclear magnetic resonance (NMR, 600 MHz, DMSO-d6) δ ppm: 3.86 (s, 3H), 6.76-6.85 (m, 1H), 7.10 (dd, J = 10.90, 2.84 Hz, 1H), 7.45 (dd, J = 8.70, 6.14 Hz, 1H).

References

[1] Patent: WO2017/220477, 2017, A1. Location in patent: Page/Page column 33

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