3-Fluoro-4-methoxyacetophenone Chemical Properties

Melting point:

92-94 °C(lit.)

Boiling point:

147-148 °C20 mm Hg(lit.)

Density 

1.1410 (estimate)

Flash point:

147-148°C/20mm

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Almost white

BRN 

2084062

CAS DataBase Reference

455-91-4(CAS DataBase Reference)

NIST Chemistry Reference

Acetophenone, 3'-fluoro-4'-methoxy-(455-91-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2914790090

MSDS

• Language:English Provider:3-Fluoro-4-methoxyacetophenone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Fluoro-4-methoxyacetophenone Usage And Synthesis

Uses

3’-Fluoro-4’methoxyacetophenone is used in the synthesis chalcones,

Preparation

Obtained by fluorination of 4-methoxyacetophenone with manganese (IV) tetrafluoride formed in situ using manganese (IV) dioxide and pyridinium polyhydrogenofluoride under very mild conditions.

General Description

3′-Fluoro-4′-methoxyacetophenone can be prepared by Friedel-Crafts reaction of o-fluoroanisole with acetic anhydride.

Synthesis

Under ice bath conditions, 6.38 g (48 mmol) of aluminum trichloride and 40 mL of methylene chloride were added to a 100 mL round bottom flask and stirred until dissolved. Subsequently, 4.68 g (60 mmol) of acetyl chloride was slowly added, keeping the reaction temperature at 5 to 10 °C. Stirring was continued at 5°C for 10 minutes, followed by the slow dropwise addition of 5.04 g (40 mmol) 2-fluoroanisole. After the dropwise addition was completed, the reaction mixture was stirred at 5°C for 1 hour. Upon completion of the reaction, the mixture was carefully poured into 100 mL of ice water to quench the reaction. The aqueous layer was extracted with dichloromethane (2 x 30 mL) and the organic phases were combined. The organic phase was washed sequentially with water (2 x 30 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was washed with petroleum ether and finally recrystallized with ethyl acetate to obtain the target product 3-fluoro-4-methoxyacetophenone in 92.4% yield.

References

[1] Patent: CN107686465, 2018, A. Location in patent: Paragraph 0041; 0053; 0054
[2] Patent: US6342510, 2002, B1. Location in patent: Page column 28
[3] Patent: US5098602, 1992, A
[4] Patent: WO2006/136829, 2006, A2. Location in patent: Page/Page column 123
[5] Journal of Organic Chemistry, 1953, vol. 18, p. 910,914

3-Fluoro-4-methoxyacetophenone(455-91-4)Related Product Information

• 4'-Hydroxyacetophenone
• 4'-(Trifluoromethyl)acetophenone
• 3-Nitroacetophenone
• (Trifluoromethoxy)benzene
• 4-(Trifluoromethoxy)aniline
• Acetophenone
• 3',5'-Dimethoxyacetophenone
• 4-Nitroacetophenone
• L-PICEIN
• 3,4-Dimethoxyacetophenone
• 4'-Methylacetophenone
• 4'-Methoxyacetophenone
• 2-Bromoacetophenone
• 3-Methoxyacetophenone
• 2'-Methoxyacetophenone
• 4-Fluoroacetophenone
• 2-Fluoro-4-methoxyacetophenone
• Fluorine