5-Fluoro-2-nitrobenzoic acid Chemical Properties

Melting point:

131-134 °C (lit.)

Boiling point:

344.2±27.0 °C(Predicted)

Density 

1.568±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.89±0.25(Predicted)

form 

Crystalline Powder

color 

White to pale yellow

InChI

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

InChIKey

GHYZIXDKAPMFCS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

320-98-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22-20/21/22

Safety Statements 

26-36-36/37/39-22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Fluoro-2-nitrobenzoic acid Usage And Synthesis

Uses

5-Fluoro-2-nitrobenzoic acid is used in the production of pharmaceuticals, dye carriers, plasticizers, fragrances and food preservatives, and is also used to improve the performance of alkyd resin coatings.

Chemical Properties

white to light yellow crystal powder

General Description

5-Fluoro-2-nitrobenzoic acid, an ortho-nitro benzoic acid derivative, can be prepared by the oxidation of 5-fluoro-2-nitrotoluene. It is an intermediate formed during the synthesis of N¹-(2,4-dichlorophenyl)-2-amino-5-fluorobenzamide. It participates in the synthesis of novel quinazolinones that are potential inhibitors of p38α mitogen-activated protein kinase (MAPK).

Synthesis

a) General procedure for the synthesis of 5-fluoro-2-nitrobenzoic acid: 3-fluorobenzoic acid (7.9 g, 56 mmol) was dissolved in concentrated sulfuric acid (50 mL), and the solution was cooled to 0 °C. Fuming nitric acid (4.7 g, 67 mmol) was added dropwise with stirring. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the mixture was carefully poured into water (750 mL) and extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 5-fluoro-2-nitrobenzoic acid as a light yellow solid (9.6 g, 52 mmol, 93% yield).1H NMR (300 MHz, d6-DMSO) data for 5-fluoro-2-nitrobenzoic acid: δ 7.66 (m, 1H), 7.74 (m, 1H), 8.17 (m, 1H) ppm.

References

[1] Patent: US5514676, 1996, A
[2] Tetrahedron, 2006, vol. 62, # 31, p. 7284 - 7292
[3] Patent: WO2006/95014, 2006, A1. Location in patent: Page/Page column 41
[4] Patent: WO2004/74218, 2004, A2. Location in patent: Page 106
[5] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 43

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