4-Fluoro-3-nitrobenzoic acid Chemical Properties

Melting point:

123-126 °C (lit.)

Boiling point:

92°C 15mm

Density 

1.5071 (estimate)

Flash point:

92°C/15mm

storage temp. 

Sealed in dry,Room Temperature

solubility 

95% ethanol: soluble50mg/mL, clear, light yellow

pka

3.54±0.10(Predicted)

form 

Powder or Crystals

color 

Light yellow to tan

Water Solubility 

insoluble

BRN 

2107562

InChI

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

InChIKey

BOJWTAQWPVBIPG-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

453-71-4(CAS DataBase Reference)

NIST Chemistry Reference

4-Fluoro-3-nitrobenzoic acid(453-71-4)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

2

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:4-Fluoro-3-nitrobenzoic acid
• Language:English Provider:ACROS
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4-Fluoro-3-nitrobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

4-Fluoro-3-nitrobenzoic acid was used:

• as starting reagent in the preparation of novel benzimidazoles having antimycobacterial activity
• in preparation of series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure
• in preparation of bis(heterocyclic) skeletal precursors for the Pictet-Spengler reaction
• in solid-phase synthesis of trisubstituted [1,3,5]triazino[1,2-a]benzimidazole-2,4(3H,10H)-diones

Synthesis

General procedure for the synthesis of 4-fluoro-3-nitrobenzoic acid from 4-fluorobenzoic acid: Potassium nitrate (39.7 g, 0.39 mol, 1.1 eq.) was added in batches to a solution of 4-fluorobenzoic acid (50.0 g, 0.36 mol, 1.0 eq.) dissolved in concentrated sulphuric acid (180 ml) under cooling in an ice bath. The reaction mixture was stirred overnight at room temperature and then slowly poured over crushed ice (800 g) under continuous stirring. The resulting mixture was allowed to stand at room temperature overnight, followed by filtration and washing of the solid product with plenty of water. Finally, treatment by azeotropic drying with toluene afforded 59.5 g (90% yield) of 4-fluoro-3-nitrobenzoic acid as a light yellow solid.1H NMR (400 MHz, DMSO-d6): δ 7.69-7.74 (m, 1H), 8.29-8.32 (m, 1H), 8.56 (d, J=7.2 Hz, 1H), 13.75 ( br s, 1H).

References

[1] Patent: US2008/249101, 2008, A1. Location in patent: Page/Page column 20
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1905 - 1917
[3] Tetrahedron Letters, 2017, vol. 58, # 43, p. 4145 - 4148
[4] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 5134 - 5144
[5] Bulletin de la Classe des Sciences, Academie Royale de Belgique, 1921, vol. <5> 7, p. 536

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