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Description
TCI C2121 4-Chloro-2-fluorobenzonitrile is a doubly halogenated benzonitrile that belongs to the family of fluorinated building blocks. Its molecule carries three functional handles at once: a nitrile group that serves as a centre for transformation, an activated fluorine atom, and a chlorine atom that acts as a coupling point. This combination makes it one of the most efficient starting materials for constructing complex molecules, because a single compound can be directed into several different synthetic branches without any need to modify the aromatic framework beforehand. Researchers in medicinal chemistry and functional materials use it to shorten reaction sequences by a meaningful number of steps.
The most notable property of this compound is the activation of the fluorine atom by the nitrile group positioned ortho to it. The nitrile withdraws electron density strongly, so the carbon bearing the fluorine becomes electrophilic and is readily displaced by nucleophiles such as amines, alkoxides, or thiolates under comparatively simple nucleophilic aromatic substitution conditions. The chlorine atom, by contrast, is far less reactive toward that pathway, so it survives intact and remains available later for palladium-catalysed cross-coupling. The nitrile group itself can subsequently be converted into other functionality, which gives the chemist a third independent point of elaboration on the same ring.
In Indonesian laboratories, this building block is typically used in university research groups, pharmaceutical development units, and materials chemistry laboratories that carry out multi-step organic synthesis. It is most often encountered in exploratory route-scouting work, in the preparation of intermediates for biologically active compounds, and in small-scale synthesis of substituted heterocycles. Because the three reactive positions can be addressed one after another, it suits laboratories that need to generate several analogues from a shared starting material.
Laboratory Applications
- Nucleophilic aromatic substitution: the nitrile-activated fluorine is displaced cleanly by amines, alkoxides, or thiolates under relatively mild SNAr conditions, giving direct access to substituted aryl products.
- Palladium-catalysed cross-coupling: the chlorine atom remains untouched during SNAr chemistry and can later be engaged as the coupling site, allowing carbon-carbon or carbon-heteroatom bond formation at a defined position.
- Medicinal chemistry intermediate synthesis: the three orthogonal handles let chemists build complex target molecules through a shorter reaction sequence than would be required from an unfunctionalised aromatic core.
- Functional materials research: the halogenated benzonitrile framework serves as a starting scaffold for materials chemists who need controlled, stepwise elaboration of an aromatic ring system.
- Analogue library preparation: because each reactive site can be addressed separately, a single batch of this compound can be branched into several structurally distinct products for comparative study.
Specifications
- Brand: TCI
- CAS Number: 57381-51-8
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Compound class: doubly halogenated benzonitrile, fluorinated building block
- Pack sizes: available in the standard TCI catalogue pack sizes for this catalogue number
- Storage: store according to the conditions stated on the manufacturer label and Safety Data Sheet
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, and incompatible materials, following the conditions given on the manufacturer label and Safety Data Sheet. Keep the material in its original supplier container or in a compatible, clearly labelled chemical container, and reseal it immediately after each use to limit moisture uptake and vapour release. Handle it inside a fume hood while wearing safety glasses, chemical-resistant gloves, and a laboratory coat. Avoid inhalation of vapour or dust and avoid contact with skin and eyes. Review the Safety Data Sheet before first use, and collect any residues and contaminated material as chemical waste for disposal through the laboratory's established waste-handling procedure.
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