3-Fluoro-4-nitrobenzoic acid Chemical Properties

Melting point:

174-175°C

Boiling point:

372.8±27.0 °C(Predicted)

Density 

1.568±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.08±0.10(Predicted)

color 

White to Light yellow to Green

InChI

InChI=1S/C7H4FNO4/c8-5-3-4(7(10)11)1-2-6(5)9(12)13/h1-3H,(H,10,11)

InChIKey

WVZBIQSKLXJFNX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

403-21-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-37/38-36-22

Safety Statements 

26-36/37/39-37

HazardClass 

IRRITANT

HS Code 

29163990

3-Fluoro-4-nitrobenzoic acid Usage And Synthesis

Uses

3-Fluoro-4-nitrobenzoic Acid is used in the synthesis of ABT-072, a non-nucleoside HCV NS5B polymerase inhibitor.

Synthesis

To a solution of 3-fluoro-4-nitrobenzyl alcohol (2.97 g) in acetone (60 ml) was added Jones reagent (13 ml), prepared from chromic acid (26.7 g) and sulfuric acid (23 ml) in water (100 ml), dropwise at 0°C. The mixture was stirred on a ice-bath for 0.5 h and quenched with isopropanol (20 ml) to be concentrated in vacuo. The residue was dissolved in ethyl acetate (30 ml) and washed with water (30 ml X 3), and brine (30 ml X 1), successively. The organic layer was dried over sodium sulfate and concentrated in vacuo to obtain a yellow solid, that was triturated with hexane. 3-fluoro-4-nitrobenzoic acid as a pale yellow solid (2.94 g, 92%).

References

[1] Patent: WO2009/130481, 2009, A1. Location in patent: Page/Page column 145
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1729 - 1744
[3] Patent: EP1820799, 2007, A1
[4] Patent: WO2006/51851, 2006, A1. Location in patent: Page/Page column 60-61
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1386 - 1391

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