1-BROMO-2,4-DIFLUORO-5-NITROBENZENE Chemical Properties

Melting point:

19°C(lit.)

Boiling point:

85°C 0,4mm

Density 

1.890±0.06 g/cm3(Predicted)

refractive index 

1.5580 to 1.5620

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump to clear liquid

color 

White or Colorless to Light yellow

InChI

InChI=1S/C6H2BrF2NO2/c7-3-1-6(10(11)12)5(9)2-4(3)8/h1-2H

InChIKey

OOUUWURPSUSDTD-UHFFFAOYSA-N

SMILES

C1(Br)=CC([N+]([O-])=O)=C(F)C=C1F

CAS DataBase Reference

345-24-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2904990090

1-BROMO-2,4-DIFLUORO-5-NITROBENZENE Usage And Synthesis

Uses

1-Bromo-2,4-difluoro-5-nitrobenzene is a nitrobenzene derivative containing fluorine and bromine atom substituents. It can be used as a pharmaceutical intermediate for the preparation of novel N2-phenylpyrimidine-2,4-diamine compounds showing effective inhibition of EGFR mutations, and thus can be effectively used in the treatment of EGFR-mutated cancers.

Synthesis

General procedure for the synthesis of 2,4-difluoro-5-bromonitrobenzene from 2,4-difluorobromobenzene: Concentrated HNO3 (34.0 mL) was added slowly and dropwise to a suspension of 1-bromo-2,4-difluorobenzene (53.0 mmol, 6.00 mL) in concentrated H2SO4 (38.5 mL) at 0 °C, ensuring that the internal temperature was maintained below 0 °C. The reaction mixture was stirred for 10 minutes with vigorous stirring. The reaction mixture was continued to be stirred at 0 °C for 10 min and subsequently poured into an ice/water mixture under vigorous stirring. The mixture was extracted with ether (ET20, 3 x 100 mL). The combined organic phases were washed sequentially with aqueous NaHCO3 (3 x 100 mL) and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by fast chromatography (eluent: EtOAc/hexane=1:9) to afford 5-bromo-2,4-difluoronitrobenzene as a yellow oil (12.2 g, 97% yield).1H NMR (400 MHz, CDCl3) δ 8.45 (t, 1H, J=7.5 Hz), 7.16 (dd, 1H, J=11.0,8.6 Hz) ; ESMS m/z: 240, 238, 223, 221, 112.

References

[1] Synthesis, 1998, # 8, p. 1101 - 1103
[2] Patent: WO2004/5257, 2004, A1. Location in patent: Page 67
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3870 - 3882
[4] Patent: US2005/154020, 2005, A1. Location in patent: Page/Page column 8
[5] Patent: US2005/154022, 2005, A1. Location in patent: Page/Page column 9

1-BROMO-2,4-DIFLUORO-5-NITROBENZENE(345-24-4)Related Product Information

• 5-Bromo-2,3-difluoro-1-nitrobenzene
• 1-BROMO-2,5-DIFLUORO-4-NITROBENZENE
• Nitrobenzene
• 5-bromo-1,3-difluoro-2-nitrobenzene
• 3-Bromo-4-fluoroaniline
• 4-Bromo-1-fluoro-2-nitrobenzene
• 3-Bromo-4-fluoronitrobenzene
• 4-Bromofluorobenzene
• 5-BROMO-2,4-DIFLUOROANILINE
• 1-Bromo-2,4-difluorobenzene
• 2,4-Difluoronitrobenzene
• 5-BROMO-2-FLUOROANILINE
• 1-BROMO-2,4-DIFLUORO-5-NITROBENZENE
• 2-BROMO-3,5-DIFLUORO-1-NITROBENZENE
• 1-BROMO-3,4-DIFLUORO-2-NITROBENZENE
• 1-BROMO-2,3-DIFLUORO-4-NITROBENZENE
• 1-BROMO-2,6-DIFLUORO-4-NITROBENZENE
• 1-BROMO-2,5-DIFLUORO-4-NITROBENZENE, TECH