Related applications of 3-Chloro-4-(trifluoromethyl)cinnamicacid(cas: 1092460-80-4)

Product Manager: Selina Zhang; Email: selina@coreychem.com

3-Chloro-4-(trifluoromethyl)cinnamic acid (CAS: 1092460-80-4) is a halogenated α,β-unsaturated carboxylic acid featuring a cinnamic acid core with chloro and trifluoromethyl substituents at the 3- and 4-positions of the phenyl ring, respectively. With the molecular formula C₁₀H₆ClF₃O₂ and a molecular weight of 250.60, this compound serves as a versatile and valuable building block in organic synthesis, medicinal chemistry, and materials science. Its α,β-unsaturated acid moiety enables diverse transformations, including conjugate additions, esterifications, amide couplings, and cycloaddition reactions, while the electron-withdrawing chloro and trifluoromethyl groups impart enhanced lipophilicity, metabolic stability, and altered electronic properties to the molecule. The compound is primarily employed in drug discovery, agrochemical research, and specialty chemical development. Its primary applications are outlined below:

1. Medicinal Chemistry & Pharmaceutical Research
Synthesis of Bioactive Molecules and Drug Candidates

3-Chloro-4-(trifluoromethyl)cinnamic acid is widely utilized as a key synthetic intermediate in the preparation of biologically active compounds. The cinnamic acid scaffold is a privileged structure found in numerous natural products and pharmaceuticals, and its functionalized derivatives exhibit a broad spectrum of pharmacological activities, including anticancer, antimicrobial, anti-inflammatory, and antioxidant properties.

CFTR Modulator Development

The compound has been identified as a potential small-molecule modulator of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR), a chloride channel that is defective in cystic fibrosis. Quinolinone-containing compounds derived from 3-chloro-4-(trifluoromethyl)cinnamic acid have demonstrated CFTR potentiator activity, supporting drug discovery efforts for respiratory diseases.

Kinase Inhibitor Scaffolds

The compound serves as a building block for the synthesis of kinase inhibitors targeting pathways involved in cancer and inflammatory diseases. Its defined substitution pattern enables the construction of inhibitor libraries with predictable vector geometry for structure-activity relationship (SAR) studies.

2. Agrochemical Research
Pesticide and Herbicide Development

Halogenated cinnamic acid derivatives are often explored for their potential as agrochemical agents, including pesticides, herbicides, and fungicides. The trifluoromethyl group is a common pharmacophore in agrochemicals, imparting enhanced metabolic stability and bioactivity, while the chloro substituent contributes to the molecule’s overall lipophilicity and target interaction properties.

Plant Growth Regulator Studies

Cinnamic acid derivatives have been investigated for their effects on plant growth and development. Researchers utilize this compound as a precursor or reference standard in studies exploring plant hormone modulation and stress response mechanisms.

3. Material Science & Specialty Chemical Applications
Synthesis of Functional Polymers

The α,β-unsaturated carboxylic acid moiety enables polymerization or copolymerization reactions, allowing the incorporation of the halogenated aromatic unit into polymeric materials. This can be used to develop polymers with tailored properties, such as enhanced thermal stability, flame retardancy, or optical characteristics.

Organic Electronics and Photovoltaics

The electron-withdrawing nature of the trifluoromethyl and chloro groups can tune the electronic properties of conjugated organic materials. This makes the compound a valuable intermediate for the synthesis of organic semiconductors, light-emitting diodes (OLEDs), and photovoltaic materials.

Liquid Crystal Intermediates

The rigid cinnamic acid core and well-defined aromatic substitution pattern make this compound a suitable intermediate for the preparation of liquid crystalline materials, which are essential components in display technologies and optical devices.

4. Organic Synthesis & Chemical Biology
Versatile Synthetic Building Block

The compound’s diverse reactivity enables a wide range of transformations, including:

• Esterification and Amidation: Conversion to esters and amides for further derivatization or library generation.

• Conjugate Addition: The α,β-unsaturated system is a Michael acceptor for nucleophiles, enabling C-C bond formation.

• Cycloaddition Reactions: Participation in cycloaddition reactions to construct more complex ring systems.

• Decarboxylative Coupling: Utilized in cross-coupling reactions to form biaryl or alkenyl products.

Probe Synthesis for Biological Studies

The compound can be used to synthesize chemical probes for studying biological pathways, including those involving cinnamic acid metabolism and signaling.

5. Handling & Storage
Storage Conditions

Store in tightly sealed containers under dry, cool, and well-ventilated conditions. Protect from moisture, excessive heat, and direct sunlight. Avoid contact with strong oxidizing agents and bases. Appropriate laboratory safety procedures should be followed during handling.

Intended Use

This product is intended strictly for laboratory research, medicinal chemistry, drug discovery, agrochemical development, and scientific investigation. It is not intended for therapeutic, diagnostic, food, or household applications without appropriate regulatory approval. Standard laboratory safety practices and protective equipment should be used during handling.

Summary

The value of 3-Chloro-4-(trifluoromethyl)cinnamic acid (CAS: 1092460-80-4) lies in its unique combination of a versatile α,β-unsaturated carboxylic acid core, strategic halogenation pattern, and the presence of a metabolically stable trifluoromethyl group. Its role as a key synthetic intermediate for CFTR modulators, kinase inhibitors, agrochemicals, and functional materials makes it an indispensable tool for medicinal chemistry, organic synthesis, and materials research. The compound supports advanced investigations into bioactive molecule development, structure-activity relationship studies, and the synthesis of next-generation specialty chemicals across multiple application areas.

For more information, please contact: selina@coreychem.com