5-FLUORO-2-METHOXYACETOPHENONE Chemical Properties

Melting point:

23 °C

Boiling point:

132 °C(Press: 13 Torr)

Density 

1.1880 g/mL at 25 °C

refractive index 

1.5180

Flash point:

110 °C

storage temp. 

Sealed in dry,Room Temperature

form 

liquid

Appearance

Colorless to off-white <23°C Solid,>23°C Liquid

CAS DataBase Reference

445-82-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-22

Safety Statements 

26-36/37/39-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2914790090

5-FLUORO-2-METHOXYACETOPHENONE Usage And Synthesis

Uses

5′-Fluoro-2′-methoxyacetophenone is used to synthesize other fluorinated compounds.

Reactions

5′-Fluoro-2′-methoxyacetophenone is a reactive intermediate that undergoes an electrophilic aromatic substitution with methanol to form the corresponding fluorinated methoxyacetophenone.

Synthesis

Step 2. A 4.1:1 mixture of 5-fluoro-2-hydroxyacetophenone (10.4 g, 61.8 mmol) and dimethyl sulfate (2.54 g, 16.5 mmol) was dissolved in acetone (50 mL) and potassium carbonate (2.50 g, 18.1 mmol) was added. Dimethyl sulfate (0.25 mL, 2.6 mmol) was then added. The reaction mixture was heated to reflux for 18 h. After cooling to room temperature, water (20 mL) was added. The mixture was stirred for 3 hours at room temperature and then partitioned between dichloromethane (50 mL) and brine (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 13.0 g (98% yield, 97% area) of 2-methoxy-5-fluoroacetophenone was obtained as a yellow oil.NMR (400 MHz, CDCl3) δppm: 2.64 (s, 3H), 3.92 (s, 3H), 6.94 (dd, J=9.09,4.04 Hz, 1H), 7.18 (ddd, J=9.09, 7.33,3.28 Hz, 1H), 7.48 (dd, J=8.97,3.16 Hz, 1H); HPLC retention time: 3.39 min; MS (ESI+) C9H9FO2 m/z 169.1 (M+H)+.

References

[1] Patent: WO2018/161008, 2018, A1. Location in patent: Paragraph 00217
[2] Journal of Organic Chemistry, 1960, vol. 25, p. 1016 - 1020
[3] Patent: US4251546, 1981, A

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