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Description
TCI F0797 2-Fluoro-4-nitrobenzoic Acid is a benzoic acid derivative that carries a fluorine atom at the ortho position and a nitro group at the para position relative to the carboxylic acid group. This arrangement of three functional groups on a single aromatic ring makes it a highly useful intermediate in stepwise organic synthesis, particularly for the construction of nitrogen-containing heterocyclic compounds. In the laboratory, this compound is frequently used as the starting point of a sequential reaction series: nucleophilic substitution at the fluorine atom, activation of the carboxylic acid group into an amide, and then reduction of the nitro group into an amine to close the ring.
Its practical value comes from the mutually reinforcing cross-activation between the functional groups. The strongly electron-withdrawing nitro group, together with the carboxylic acid group positioned next to the fluorine atom, leaves the fluorine-bearing position highly susceptible to attack by nucleophiles such as amines, alkoxides, and thiols, so that nucleophilic aromatic substitution proceeds under relatively mild conditions. Once that step is complete, the nitro group can be reduced to an amine and cyclized together with the carboxylic acid group to form benzimidazolone, quinazolinone, or benzodiazepinone frameworks.
The compound is generally supplied as a white to yellowish crystalline solid that is stable under ordinary laboratory conditions. In Indonesian laboratories, it is typically used in medicinal chemistry and organic synthesis groups at universities and research institutes, as well as in pharmaceutical and fine chemical development work where nitrogen heterocycle scaffolds are assembled from simple aromatic starting materials. Its handling as a stable crystalline solid makes it convenient for routine weighing and reaction setup on the bench.
Laboratory Applications
- Nucleophilic aromatic substitution studies: the activating nitro and carboxylic acid groups make the fluorine position readily displaced by amines, alkoxides, and thiols under relatively mild reaction conditions.
- Benzimidazolone synthesis: the ring can be closed after reducing the nitro group to an amine and coupling it with the adjacent carboxylic acid functionality of the molecule.
- Quinazolinone scaffold construction: the compound provides all three handles needed for amide formation, nitro reduction, and subsequent ring closure in one aromatic starting material.
- Benzodiazepinone framework preparation: sequential substitution, amidation, and reductive cyclization steps build the seven-membered nitrogen heterocycle from this single fluorinated building block.
- Medicinal chemistry intermediate work: the compound serves as a stepwise entry point for assembling nitrogen-containing heterocyclic cores during exploratory organic synthesis and analogue preparation.
Specifications
- Brand: TCI
- CAS Number: 403-24-7
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Pack sizes: available in standard TCI research-scale packaging; please confirm the pack size required when ordering
- Physical form: white to yellowish crystalline solid
- Storage: store in a cool, dry place in a tightly closed container
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated area, away from moisture and from strong bases, strong oxidizing agents, and sources of heat or ignition. Keep the material in its original tightly sealed container or in a comparable chemically resistant, well-labelled vessel, and close it promptly after each weighing to limit moisture uptake. Handle the solid inside a fume hood and wear standard personal protective equipment, including safety goggles, chemical-resistant gloves, and a laboratory coat, to avoid contact with skin and eyes and inhalation of dust. As with any nitroaromatic carboxylic acid, avoid generating dust, wash hands thoroughly after handling, and dispose of residues and contaminated materials according to institutional chemical waste procedures.
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