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Description
TCI D4156 trans-3,5-Difluorocinnamic Acid is a fluorinated cinnamic acid carrying two fluorine atoms at the 3 and 5 positions of the aromatic ring, together with a side-chain double bond in the defined trans configuration. It is classified as a fluorinated building block because it serves as a starting scaffold that presents three reactive handles at once: the carboxylic acid group, the conjugated double bond, and the aromatic ring that has already been substituted with fluorine. This combination makes it an efficient reagent for researchers who wish to introduce a fluoroaromatic motif directly into a target molecule.
The properties that make it a preferred choice centre on the influence of the two fluorine atoms, which are strongly electron-withdrawing yet small in size. They raise the acidity of the carboxylic acid group, alter the electron distribution across the ring, and improve the metabolic stability of derived compounds without adding meaningful steric bulk. The well-defined trans configuration provides geometric certainty, an important advantage for syntheses in which stereochemistry must remain under control. The symmetrical substitution pattern at the 3 and 5 positions also simplifies spectral interpretation, particularly in fluorine and proton NMR analysis.
In Indonesian laboratories, this material is typically used in university research groups, pharmaceutical and agrochemical research units, and materials chemistry laboratories that carry out fluorine-containing organic synthesis on a research scale. It is normally handled at the bench in modest quantities as an intermediate within a multi-step synthetic route, supported by routine spectroscopic verification. Its supply as a packaged research chemical from TCI suits laboratories that require a consistent, ready-to-use starting scaffold rather than preparing the fluorinated framework in house.
Laboratory Applications
- Fluorinated building block synthesis — the pre-installed 3,5-difluoro aromatic ring lets researchers introduce a fluoroaromatic motif directly into a target molecule without carrying out a separate fluorination step.
- Medicinal chemistry intermediates — the electron-withdrawing fluorine atoms improve the metabolic stability of derived compounds while adding almost no steric bulk, a combination valued in drug-discovery scaffolds.
- Carboxylic acid derivatisation — the carboxylic acid group provides a straightforward reactive handle for amidation, esterification, and coupling chemistry within multi-step synthetic sequences on the bench.
- Conjugate addition and double-bond chemistry — the conjugated trans double bond offers a second reactive site, and its defined geometry gives certainty in syntheses where stereochemistry must be controlled.
- NMR method development and structural verification — the symmetrical substitution at positions 3 and 5 simplifies spectral interpretation, making it a convenient reference substrate for fluorine and proton NMR analysis.
Specifications
- Brand: TCI
- CAS number: 147700-58-1
- Catalogue code: D4156
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Pack sizes: supplied in standard TCI research-scale packaging; available pack sizes on request
- Storage: keep in a cool, dry place in the tightly closed original container
Handling and Storage
Store the material in a cool, dry, well-ventilated area, keeping the original TCI container tightly closed and protected from moisture, direct sunlight, and heat sources. Amber or opaque glass containers with chemically resistant closures are suitable for any transfer or subdivision, and containers should be clearly labelled with the substance name and CAS number. Handle the solid in a fume hood using a laboratory coat, chemical splash goggles, and appropriate chemical-resistant gloves, since organic acids may irritate skin, eyes, and the respiratory tract. Avoid generating or inhaling dust, keep the substance away from strong bases and oxidising agents, and wash hands thoroughly after handling. Consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials through the laboratory's chemical waste system in line with local regulations.
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