3-FLUORO-4-METHYLANISOLE Chemical Properties

Boiling point:

63.5-64°C

Density 

1.046±0.06 g/cm3(Predicted)

refractive index 

1.4909

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

CAS DataBase Reference

405-06-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

F

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazard Note 

Flammable

HS Code 

2909309090

3-FLUORO-4-METHYLANISOLE Usage And Synthesis

Application

Studies have reported that 3-fluoro-4-methyl anisole can be used to prepare a diarylphosphine ligand, L10b.

Reactions

3-Fluoro-4-methylanisole is a nucleophilic, ring substituted electron acceptor that can be activated by electron donors. The nitro group and the electron donating substituents on the ring are important for this reactivity. 3-Fluoro-4-methylanisole can form substitution products with methyl or formyl groups in the presence of a strong base such as palladium, 3-fluoro-4-methylphenol, or nitro groups. This reactivity is regiospecific, meaning that the substitution will only occur at one of two possible sites on the ring. 3-Fluoro-4-methylanisole's chemical properties give it both activating and deactivating properties in organic reactions.

Synthesis

The general procedure for the synthesis of 3-fluoro-4-methylanisole from 5-methoxy-2-methylaniline was as follows: a mixed system of 5-methoxy-2-methylaniline (5.0 g; 36 mmol), concentrated hydrochloric acid (7.6 mL, 12 M solution; 91 mmol), and deionized water (11 mL) was heated and stirred at 60 °C for 15 min until complete dissolution. After the reaction solution was cooled to 0 °C, aqueous sodium nitrite (2.5 g; 36 mmol) was slowly added dropwise to control the internal temperature ≤7 °C. The reaction solution was then stirred at 0 °C for 15 min. The reaction solution was continued to be stirred at 0 °C for 30 min, followed by cautious addition of pre-cooled tetrafluoroboric acid solution (5.3 mL, 48% solution; 40 mmol). The reaction mixture was stirred at 0 °C for 20 min before the resulting brown solid was collected by filtration and washed sequentially with ice water (3 × 10 mL) and deionized water (2 × 10 mL). The solid was dried under high vacuum for 20 h. The solid was then heated with a heat gun until the release of white fumes of boron trifluoride was stopped. The resulting brown oil was extracted with ethyl acetate and water in liquid-liquid extraction, and the organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure, and finally purified by short distillation to obtain the colorless oily product 3-fluoro-4-methylanisole (1.6 g; 31% yield).

References

[1] Patent: US6414002, 2002, B1

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