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Description
3'-Fluoro-4'-hydroxyacetophenone is an aromatic building block that combines an acetyl group, a phenolic hydroxy group, and a fluorine atom on a single benzene ring. This combination of three functional groups gives synthetic chemists three distinct points of attack, each with different reactivity: an electrophilic ketone, a phenol that can be etherified or esterified, and a fluorine atom that modulates the electron density of the ring. In the laboratory, this TCI material frequently serves as a precursor for constructing chalcone, flavone, and chromanone frameworks, as well as a wide range of fluorinated aromatic-core molecules of interest in medicinal chemistry and materials research.
The property that makes it a practical choice is the versatility of its reactivity under ordinary laboratory conditions. The acetyl group can undergo Claisen–Schmidt condensation with aromatic aldehydes to give chalcones, be halogenated at the alpha position, be reduced to a secondary alcohol, or be converted into heterocyclic rings through reaction with hydrazine and hydroxylamine. The phenol group allows for the installation of protecting groups, selective alkylation, and intramolecular cyclization. The presence of fluorine adjacent to the phenol lowers the pKa of that phenol and alters hydrogen-bonding strength, giving the chemist an additional handle for tuning molecular behaviour.
In Indonesian laboratories, this building block is typically used in synthetic organic chemistry groups at universities and research institutes, as well as in industrial R&D units developing fluorinated compounds. It is commonly employed in postgraduate research on chalcone and flavonoid analogues, in medicinal chemistry programmes screening fluorinated aromatic scaffolds, and in materials work where the fluorine substituent is used to adjust the electronic character of the aromatic core.
Laboratory Applications
- Chalcone synthesis: the acetyl group condenses readily with aromatic aldehydes under Claisen–Schmidt conditions, giving fluorinated chalcone analogues without requiring specialised equipment or unusual reagents.
- Flavone and chromanone construction: the ortho relationship between the phenol and the acetyl group supports the cyclization routes that build these oxygen heterocycles directly from a single starting material.
- Heterocycle formation: reaction of the ketone with hydrazine or hydroxylamine delivers pyrazole and isoxazole rings, letting one building block feed several different heterocyclic scaffold programmes.
- Medicinal chemistry scaffold work: the fluorine atom adjusts ring electron density and phenol acidity, which is useful when researchers are tuning the properties of aromatic lead structures.
- Selective phenol derivatisation: the hydroxy group accepts protecting groups, alkylation, and esterification, allowing chemists to modify one site while leaving the ketone available for later transformation.
Specifications
- Brand: TCI
- CAS number: 403-14-5
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Chemical name: 3'-Fluoro-4'-hydroxyacetophenone
- Pack sizes: available in standard laboratory research pack sizes; please confirm the packaging option required when ordering
- Storage: store in a cool, dry place in a tightly closed container, protected from light
Handling and Storage
Store the material in a cool, dry area in its original tightly closed container, kept away from direct sunlight, heat sources, and moisture. Amber glass bottles or the manufacturer's original packaging are suitable, since phenolic compounds can discolour on prolonged exposure to light and air. Handle inside a fume hood using gloves, safety glasses, and a laboratory coat, and avoid generating dust or inhaling vapour. Weigh out portions promptly and reseal the container to limit atmospheric exposure. Keep the material separate from strong oxidising agents and strong bases, label all working containers clearly, and consult the manufacturer's safety data sheet before first use and before any disposal of residues.
