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| | 4-Fluoro-3-nitrobenzoic acid Basic information |
| | 4-Fluoro-3-nitrobenzoic acid Chemical Properties |
| Melting point | 123-126 °C (lit.) | | Boiling point | 92°C 15mm | | density | 1.5071 (estimate) | | Fp | 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) |
| Hazard Codes | Xn,Xi | | Risk Statements | 22-36/37/38 | | Safety Statements | 26-36-24/25 | | WGK Germany | 2 | | HazardClass | IRRITANT | | HS Code | 29163990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 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 |
| | 4-Fluoro-3-nitrobenzoic acid Preparation Products And Raw materials |
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