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Description
TCI D4048 2,6-Dichlorocinnamic Acid is a substituted cinnamic acid compound carrying two chlorine atoms at the ortho positions of the aromatic ring, which places it in the class of non-heterocyclic building blocks. In organic synthesis laboratories, this material serves as a starting scaffold that already carries two functional handles at once: a conjugated double bond and a carboxylic acid group. That combination means it can be taken directly into amidation, esterification, conjugate addition, or further downstream transformations without having to construct the carbon framework from scratch, making synthetic routes more concise and easier to reproduce from one operator to another.
The characteristic that makes this compound a frequent choice is its 2,6-dichloro substitution pattern. The two chlorines at the ortho positions impose steric hindrance that forces the aromatic ring to twist relative to the vinyl plane, so the conformational profile and reactivity of the molecule differ from those of ordinary cinnamic acid. The chlorine atoms are also electron-withdrawing and, at the same time, act as anchor points for further modification through transition-metal-catalysed coupling reactions. Its carboxylic acid group is readily activated into an acid chloride or an active ester, giving researchers a wide range of options for extending the molecule.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, medicinal chemistry, and materials chemistry, as well as in industrial R&D units developing new candidate molecules. It is generally purchased in research-scale quantities for method development, route scouting, and the preparation of derivative libraries, where a defined, ready-to-use starting scaffold shortens the experimental timeline and keeps results comparable between batches and between operators.
Laboratory Applications
- Amidation reactions: the carboxylic acid group is readily activated into an acid chloride or an active ester, so the compound can be coupled directly with a range of amine partners.
- Esterification: the same carboxylic acid handle allows straightforward conversion into esters, giving a simple route to derivatives without modifying the aromatic core or the conjugated system.
- Conjugate addition chemistry: the double bond conjugated to the carboxylic acid provides an electrophilic site suitable for Michael-type additions and related carbon–heteroatom or carbon–carbon bond formations.
- Transition-metal-catalysed coupling: the two ortho chlorine atoms serve as anchor points for further modification, letting researchers elaborate the aromatic ring after the initial scaffold has been installed.
- Conformational and reactivity studies: the twist between the aromatic ring and the vinyl plane makes this compound useful for comparing steric and electronic effects against unsubstituted cinnamic acid.
Specifications
- Brand: TCI
- Product code: D4048
- CAS number: 5345-89-1
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in research-scale laboratory pack sizes; please confirm the currently offered packaging when ordering
- Storage: keep in a tightly closed container, stored cool and dry away from direct sunlight
Handling and Storage
Store the material in its original tightly closed container, in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and moisture. Glass or chemically compatible sealed containers are appropriate, and the container should be reclosed immediately after each use to limit exposure to humid air. Handle the compound in a fume hood using standard laboratory personal protective equipment, including safety glasses, gloves, and a laboratory coat, and avoid contact with skin, eyes, and inhalation of dust. Keep it separated from strong bases and strong oxidising agents, use clean and dry spatulas when weighing to prevent cross-contamination, and always consult the manufacturer's safety data sheet before handling, use, or disposal.
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