2-BROMO-5-FLUORO-4-METHYLANILINE Chemical Properties

Melting point:

39-41°C

Boiling point:

245.3±35.0 °C(Predicted)

Density 

1.589±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

1.95±0.10(Predicted)

CAS DataBase Reference

202865-78-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2921430090

2-BROMO-5-FLUORO-4-METHYLANILINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-bromo-5-fluoro-4-methylaniline from 3-fluoro-4-methylaniline: Step A- Synthesis of compound 28B: Compound 28A (3-fluoro-4-methylaniline, 6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) were dissolved in anhydrous dichloromethane (130 mL), and the mixture was cooled to -15 °C in a salt-ice bath. Subsequently, a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL) was slowly added dropwise. After the dropwise addition was completed, the reaction temperature was maintained at -15 °C and stirring was continued for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of ice water (100 mL) to the reaction mixture and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude product compound 28B (2-bromo-5-fluoro-4-methylaniline, 11.0 g, quantitative yield), which could be used in subsequent steps without further purification.

References

[1] Patent: WO2009/32123, 2009, A2. Location in patent: Page/Page column 158
[2] Patent: WO2009/32125, 2009, A1. Location in patent: Page/Page column 98
[3] Patent: WO2009/32124, 2009, A1. Location in patent: Page/Page column 198-199
[4] Patent: WO2009/152200, 2009, A1. Location in patent: Page/Page column 65
[5] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 3, p. 244 - 248

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