5-Bromo-2-fluoro-4-methylaniline Chemical Properties

Boiling point:

244℃

Density 

1.589

Flash point:

101℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.56±0.10(Predicted)

form 

crystalline powder

color 

Creamy goldfaint tan, tiny flakes

Safety Information

HS Code 

2921420090

5-Bromo-2-fluoro-4-methylaniline Usage And Synthesis

Uses

5-?Bromo-?2-?fluoro-?4-?methylaniline is a reagent used in the synthesis of Pan-RAF inhibitors which may be used in the treatment of cancers.

Synthesis

Step b: Synthesis of 5-bromo-2-fluoro-4-methylaniline To a stirred solution of 1-bromo-4-fluoro-2-methyl-5-nitrobenzene (18.0 g, 0.230 mol) in ethanol (300 mL) was added SnCl2-2H2O (51.8 g, 0.230 mol). The reaction mixture was heated to reflux and maintained for 3 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was dissolved in ice water and the pH was adjusted to 7 with saturated aqueous NaHCO3. The precipitated solid was collected by filtration and the filtrate was extracted with dichloromethane (200 mL × 3). The organic phases were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: petroleum ether/EtOAc = 10/1) to afford 5-bromo-2-fluoro-4-methylaniline (5.0 g, two-step yield 30%). 1H NMR (400 MHz, CDCl3) δ 6.96 (d, J = 8.8 Hz, 1H), 6.86 (d, J = 11.6 Hz, 1H), 3.64 (br, 2H), 2.26 (s, 3H). MS (ESI) m/z (M + H+) 204.0.

References

[1] Patent: WO2013/134298, 2013, A1. Location in patent: Page/Page column 42
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[3] Patent: WO2013/134243, 2013, A1. Location in patent: Page/Page column 9-11
[4] Patent: US2008/9524, 2008, A1. Location in patent: Page/Page column 407
[5] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1251

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