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Description
TCI D4115 trans-2,6-Difluorocinnamic Acid is a fluorinated cinnamic acid derivative that carries two fluorine atoms at the ortho positions of the benzene ring, together with a double bond of defined trans geometry along its acrylate side chain. As a fluorinated synthetic building block, this compound plays an important role in the preparation of molecules that require deliberate adjustment of electronic and metabolic properties. In medicinal chemistry laboratories, the cinnamic acid motif is a framework commonly encountered in bioactive compounds, while the addition of fluorine provides a directed means of tuning the acidity, stability, and binding affinity of the final molecule.
The characteristic that makes this material a preferred choice is the strong influence exerted by the two ortho fluorine atoms on the aromatic ring. Fluorine is highly electronegative, so it withdraws electron density, lowers the pKa value of the carboxylic acid group, and activates the ring toward nucleophilic aromatic substitution where that reactivity is required. The two fluorine atoms also hinder metabolic oxidation at those positions, a common strategy in drug design. The well-defined trans geometry gives the molecule a rigid and predictable shape, which is important for fitting into protein binding pockets, while the carboxylic acid group offers a convenient handle for further derivatisation.
In Indonesian laboratories, this building block is typically used in university research groups, pharmaceutical research units, and contract synthesis laboratories that carry out multi-step organic preparations. It is generally handled at bench scale for exploratory route development, analogue series preparation, and reference material synthesis, where a well-characterised starting material from an established supplier reduces variability between batches. Researchers usually order it alongside coupling reagents and other fluorinated intermediates as part of a planned synthetic campaign rather than as a routine bulk consumable.
Laboratory Applications
- Medicinal chemistry building block synthesis: the fluorinated cinnamic acid scaffold allows researchers to introduce a rigid, electron-poor aromatic unit into candidate molecules while tuning acidity and metabolic stability in a controlled way.
- Amide and ester derivatisation: the free carboxylic acid group provides a direct handle for coupling reactions, letting laboratories build focused analogue libraries from a single, consistently supplied fluorinated starting material.
- Nucleophilic aromatic substitution studies: the two ortho fluorine atoms activate the ring toward displacement chemistry, making this compound a practical substrate for investigating substitution reactivity and preparing further functionalised aromatics.
- Structure-activity relationship investigations: the defined trans geometry gives a predictable molecular shape, so researchers can study how conformational rigidity and fluorine substitution affect binding to target protein pockets.
- Reference and intermediate preparation: as a well-defined fluorinated building block, it serves as a starting material or comparison compound in multi-step synthetic routes requiring reproducible material between experimental batches.
Specifications
- Brand: TCI
- CAS number: 102082-89-3
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Product code: D4115
- Pack sizes: available in standard TCI research pack sizes; please confirm the currently listed options when ordering
- Storage note: store in a cool, dry place in a tightly closed container, following the supplier documentation supplied with the product
Handling and Storage
Store this material in a tightly closed original container in a cool, dry, and well ventilated area, away from direct sunlight, moisture, heat sources, and incompatible substances such as strong bases and strong oxidising agents. Amber glass or the supplier's own container is suitable for keeping the compound protected during storage. Handle the material inside a fume hood using appropriate personal protective equipment, including safety glasses, a laboratory coat, and chemically resistant gloves. Avoid generating dust, avoid inhalation and contact with skin and eyes, and keep containers closed when not in active use. Always consult the manufacturer's Safety Data Sheet before opening, weighing, or transferring the compound, and follow institutional procedures for chemical waste disposal.
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