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Description
TCI D3559 2',6'-Difluoroacetophenone is a fluorinated aromatic ketone that serves as a versatile intermediate in organic synthesis. Structurally, the molecule is an acetophenone bearing two fluorine atoms at both ortho positions of the aromatic ring. The methyl ketone carbonyl group provides a reactive center for enolate formation, condensation, and reduction, while the symmetrical ortho-fluorination pattern imparts a distinctive electronic character. In the laboratory, this compound acts as an efficient starting material for constructing a wide range of heterocycles as well as target molecules that require a fluorinated aromatic ring.
The properties that make it a widely preferred choice are the combination of reactivity and the electronic influence of the fluorine atoms. The two ortho fluorines withdraw electron density, making the carbonyl more electrophilic and the alpha protons more readily abstracted, which accelerates aldol and Claisen-Schmidt condensations as well as enol ether formation. Fluorine also contributes metabolic stability and measurable lipophilicity to the final molecule, two attributes that are highly sought after in drug candidate design. The presence of fluorine atoms brings an additional analytical advantage, because reactions can be monitored directly by interference-free fluorine-19 NMR spectroscopy.
In Indonesian laboratories, this building block is typically used in academic and industrial research settings where fluorinated scaffolds are required. It suits synthetic chemistry groups in universities, pharmaceutical research and development units, and contract research laboratories that prepare heterocyclic intermediates on a bench scale. Because it is supplied by TCI as a catalogue building block, it is generally ordered for exploratory route development, method optimisation, and small-scale preparation of fluorinated target compounds rather than for bulk manufacturing.
Laboratory Applications
- Heterocycle construction: the activated methyl ketone readily undergoes cyclisation chemistry, allowing researchers to assemble fluorinated pyrazoles, pyrimidines, and related ring systems from a single accessible starting material.
- Aldol and Claisen-Schmidt condensation: the electron-withdrawing ortho fluorines increase alpha-proton acidity, so enolate generation and subsequent carbon-carbon bond formation proceed under milder and more reproducible reaction conditions.
- Medicinal chemistry intermediate synthesis: the difluorinated aromatic ring transfers metabolic stability and controlled lipophilicity into drug-like target molecules, making this ketone valuable for structure-activity relationship studies.
- Carbonyl reduction and derivatisation studies: the ketone functionality can be reduced or converted into alcohols, oximes, and imines, giving synthetic groups a flexible platform for preparing diverse fluorinated derivatives.
- Fluorine-19 NMR reaction monitoring: the two fluorine atoms provide clean, interference-free spectroscopic handles, letting analysts follow conversion and by-product formation directly without additional labelling or derivatisation steps.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- Product code: D3559
- CAS number: 13670-99-0
- Chemical name: 2',6'-Difluoroacetophenone
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Pack sizes: available in standard TCI catalogue research pack sizes; please refer to the current listing for the options offered
- Storage: keep in the tightly closed original container, protected from light and moisture, in accordance with the manufacturer's stated storage conditions
Handling and Storage
Store the material in its original tightly closed container in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, ignition sources, and incompatible chemicals such as strong oxidising agents and strong bases. Chemically resistant amber glass containers with tight-fitting caps are suitable for storage and dispensing, and the container should be resealed immediately after use to limit moisture uptake and vapour release. All handling should take place in a functioning fume hood, using safety goggles, chemically resistant gloves, and a laboratory coat. Ground and bond containers where appropriate, avoid inhalation of vapours and contact with skin or eyes, and keep the workspace free of open flames. Always consult the manufacturer's Safety Data Sheet before use, and dispose of residues and contaminated materials as chemical waste according to applicable institutional and local regulations.
