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

Boiling point:

364.5±37.0 °C(Predicted)

Density 

1.896±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

-2.19±0.14(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C6H4BrFN2O2/c7-3-1-6(10(11)12)4(8)2-5(3)9/h1-2H,9H2

InChIKey

PKDUOURYTVRBLI-UHFFFAOYSA-N

SMILES

C1(N)=CC(F)=C([N+]([O-])=O)C=C1Br

Safety Information

HS Code 

2921410090

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

Uses

2-Bromo-5-fluoro-4-nitroaniline is a polysubstituted aniline compound containing substituents such as bromine, nitro and fluorine atoms in the 2, 4 and 5 positions of the benzene ring, respectively. This product can be used as an intermediate for Tezacaftor, a cystic fibrosis (CF) combination used to treat patients 6 years of age and older.

Synthesis

Bromine (2.15 mL, 42.2 mmol) was added slowly and dropwise to a mixed solution of 3-fluoro-4-nitroaniline (6.5 g, 42.2 mmol) in acetic acid (80 mL) and chloroform (25 mL) at 0 °C. The reaction mixture was stirred at room temperature for 2 hours and then poured into ice water. The pH of the mixture was adjusted to 8.0-9.0 with 10% aqueous sodium hydroxide solution under cooling in an ice bath, followed by extraction with ethyl acetate (50 mL × 3). The organic phases were combined, washed sequentially with water (80 mL × 2) and saturated saline (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-bromo-5-fluoro-4-nitroaniline (9 g, 90% yield). The product was characterized by 1H-NMR (400 MHz, DMSO-d6): δ 8.26 (d, J=8.0 Hz, 1H), 7.07 (brs, 2H), 6.62 (d, J=9.6 Hz, 1H).

References

[1] Patent: US2007/244159, 2007, A1. Location in patent: Page/Page column 112-113
[2] Patent: US2011/98311, 2011, A1
[3] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1640; 1979
[4] Patent: WO2010/53471, 2010, A1. Location in patent: Page/Page column 56-57
[5] Patent: WO2016/109362, 2016, A1. Location in patent: Paragraph 00168

2-Bromo-5-fluoro-4-nitroaniline(952664-69-6)Related Product Information

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• 2-Bromo-3,5-dichloropyridine
• 2-Bromopyridine-4-carboxylic acid
• 3-Amino-2-bromopyridine
• 2-Bromo-3-fluoropyridine
• 2-Bromo-4-chloropyridine
• 2-Bromo-3-trifluoromethylpyridine
• 2-Bromo-5,6-diphenylpyrazine
• 2-Bromo-4-fluoropyridine
• 2-Bromo-4-nitroimidazole
• 2-Bromo-3-methylbenzaldehyde