| Identification | More | [Name]
4-Fluoro-3-nitrobenzoic acid | [CAS]
453-71-4 | [Synonyms]
3-NITRO-4-FLUOROBENZOIC ACID
4-FLUORO-3-NITROBENZOIC ACID
BUTTPARK 32\01-78
RARECHEM AL BO 0969
TIMTEC-BB SBB008336
Benzoic acid, 4-fluoro-3-nitro-
p-Fluoro-3-nitrobenzoic acid
4-Fluoro-3-Nitrobenzoic acid 3-Nitro-4-Fluorobenzoic acid
4-Fluoro-3-nitrobenzoic
4-Fluoro-3-nitrobenzoic acid 99%
4-Fluoro-3-nitrobenzoicacid99%
4-Fluoro-3-nitrobenzotc acid
4-Carboxy-2-nitrofluorobenzene | [EINECS(EC#)]
207-221-3 | [Molecular Formula]
C7H4FNO4 | [MDL Number]
MFCD00007058 | [Molecular Weight]
185.11 | [MOL File]
453-71-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [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 | [form ]
Powder or Crystals | [pka]
3.54±0.10(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [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 |
|
|