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

Melting point:

86-90 °C (lit.)

Boiling point:

266.3±35.0 °C(Predicted)

Density 

1.589±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.44±0.10(Predicted)

form 

Solid

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C7H7BrFN/c1-4-2-6(9)5(8)3-7(4)10/h2-3H,10H2,1H3

InChIKey

DNCLVDGUXUSPTL-UHFFFAOYSA-N

SMILES

C1(N)=CC(Br)=C(F)C=C1C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2921420090

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

Chemical Properties

light brown solid

Uses

5-Bromo-4-fluoro-2-methylaniline is used to prepare 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran derivatives as non-nucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase.

Synthesis

The general procedure for the synthesis of 5-bromo-4-fluoro-2-methylaniline from 2-nitro-4-bromo-5-fluorotoluene was as follows: a mixture of iron powder (17.8 g, 318 mmol) and ammonium chloride (5.10 g, 95.4 mmol) in water (100 mL) was heated to reflux for 30 minutes. Subsequently, 4-bromo-3-fluoro-6-nitrotoluene (18.6 g, 79.5 mmol) was slowly added to this hot mixture and the reaction mixture was continued to reflux for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate (3 x 200 mL). The organic phases were combined, washed sequentially with water (3 × 300 mL) and brine (300 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by fast column chromatography (silica gel as stationary phase and hexane solution of 20% ethyl acetate as eluent) to afford 11.7 g of 5-bromo-4-fluoro-2-methylaniline as a light yellow solid in 72% yield. The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 6.82 (m, 2H), 3.49 (bs, 2H), 2.11 (s, 3H).

References

[1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 321 - 327
[2] Patent: WO2003/99824, 2003, A1. Location in patent: Page 32
[3] Patent: WO2003/99275, 2003, A1. Location in patent: Page 65
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 2, p. 457 - 460
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 26, p. 6603 - 6608

5-BROMO-4-FLUORO-2-METHYLANILINE(627871-16-3)Related Product Information

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• AKOS 91776
• 5-BROMO-4-FLUORO-2-METHYLANILINE
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