2-BROMO-5-FLUORO-4-METHYLANILINE

2-BROMO-5-FLUORO-4-METHYLANILINE Property

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

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2921430090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

2-BROMO-5-FLUORO-4-METHYLANILINE Chemical Properties,Usage,Production

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