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

Melting point:

130 °C

Boiling point:

354.8±37.0 °C(Predicted)

Density 

1.412±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

2.31±0.10(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C7H7FN2O3/c1-13-7-2-4(8)6(10(11)12)3-5(7)9/h2-3H,9H2,1H3

InChIKey

FYSIGSQCZXQTIH-UHFFFAOYSA-N

SMILES

C1(N)=CC([N+]([O-])=O)=C(F)C=C1OC

Safety Information

HS Code 

2921420090

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

Uses

4-Fluoro-2-methoxy-5-nitroaniline is used as a reagent for preparing the anticancer drug Mereletinib.

Synthesis

4-FLUORO-2-METHOXYANILINE(551 mg, 3.90 mmol) is dissolved in dichloromethane (39.0 mL), concentrated sulfuric acid (1.85 mL) is added dropwise with stirring under ice-cooling, and then concentrated nitric acid (267 μL, 5.85 mmol) is added dropwise. After stirring for 3 hours under ice-cooling, saturated aqueous sodium bicarbonate was added until pH 8 was reached. After washing with saturated aqueous sodium bicarbonate solution, washing with saturated brine, the organic layer was dried over sodium sulfate and evaporated under reduced pressure to obtain 675 mg of the 4-fluoro-2-Methoxy-5-nitroaniline (yield 93%).

References

[1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2898 - 2901
[2] Patent: WO2017/120429, 2017, A1. Location in patent: Page/Page column 340
[3] Patent: CN105524068, 2016, A. Location in patent: Paragraph 0181; 0183
[4] Patent: CN105884695, 2016, A. Location in patent: Paragraph 0233; 0234; 0235
[5] Patent: US2017/8889, 2017, A1. Location in patent: Paragraph 0135; 0138

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