Related applications of TRANS-3-(TRIFLUOROMETHYL)CINNAMOYL CHLORIDE(cas: 64379-91-5)

TRANS-3-(TRIFLUOROMETHYL)CINNAMOYL CHLORIDE (CAS: 64379-91-5), also known as (E)-3-(3-(trifluoromethyl)phenyl)acryloyl chloride or m-trifluoromethylcinnamoyl chloride, is an α,β-unsaturated acyl chloride featuring a cinnamoyl core with a trifluoromethyl substituent at the meta position of the phenyl ring. With the molecular formula C₁₀H₆ClF₃O and a molecular weight of 234.60 g/mol, this compound typically presents as a clear, brown to colorless liquid at room temperature (melting point: 28-31 °C). The electron-withdrawing trifluoromethyl group significantly modulates the compound’s polarity, lipophilicity, and binding affinity to biological targets. As a highly reactive acid chloride, it serves as a versatile acylating agent for introducing the trans-3-(trifluoromethyl)cinnamoyl moiety into target molecules. The compound is intended strictly for laboratory research, drug discovery, and chemical synthesis applications. Its primary applications are outlined below:

1. Organic Synthesis & Intermediate Applications

trans-3-(Trifluoromethyl)cinnamoyl chloride serves as an essential intermediate in the synthesis of various biologically active compounds. Its acyl chloride functionality readily participates in nucleophilic substitution reactions, making it valuable for creating amides (via reaction with amines), esters (via reaction with alcohols), and thioesters (via reaction with thiols). The compound is widely utilized in multi-step organic synthesis pathways for the facile introduction of the trans-3-(trifluoromethyl)cinnamoyl group, which is valuable for functionalizing molecules. Its applications extend to the synthesis of polymers, semiconductor materials, and sensor materials.

2. Pharmaceutical Research & Drug Discovery

The compound is utilized in the synthesis of pharmaceutical agents due to its ability to form stable amides and esters. Research indicates that derivatives of cinnamic acid have shown significant biological activities, including enzyme inhibition. Studies have demonstrated that certain cinnamic acid derivatives exhibit selective inhibition of monoamine oxidase (MAO), which is crucial for developing treatments for neurodegenerative diseases such as Alzheimer’s disease. The trifluoromethyl group affects polarity and lipid solubility, making this compound particularly valuable in drug research. It is classified as a pharmaceutical intermediate and serves as a building block in the discovery and development of new pharmaceutical agents.

3. Anticancer Research

Studies suggest that trans-3-(Trifluoromethyl)cinnamoyl chloride can inhibit cancer cell proliferation and induce apoptosis in various cancer cell lines. Research indicated that certain derivatives could induce morphological changes and enhance caspase-3 activity in breast cancer cells, suggesting their potential as anticancer agents. The trifluoromethyl group enhances its anticancer efficacy.

4. Antioxidant Research

Cinnamic acid derivatives, including trans-3-(Trifluoromethyl)cinnamoyl chloride, have shown potential antioxidant properties. This activity is attributed to their ability to scavenge free radicals, which helps mitigate oxidative stress linked to chronic diseases.

5. Organic Photoelectric Materials

The compound is employed in the development of organic photoelectric materials, which are crucial for applications in photovoltaics and organic light-emitting diodes (OLEDs). Its unique electronic properties make it suitable for enhancing the efficiency of these materials. It is also used in the preparation of semiconductor materials.

6. Agricultural Chemistry & Pesticide Synthesis

trans-3-(Trifluoromethyl)cinnamoyl chloride is utilized in the synthesis of pesticides, contributing to agricultural chemistry by providing effective solutions for pest control.

7. Structure-Activity Relationship (SAR) Studies

The introduction of functional groups significantly affects the biological activity of cinnamic acid derivatives. The trifluoromethyl group enhances lipophilicity and improves binding affinity to biological targets. Hydroxyl group addition has been shown to increase MAO-B inhibition. These SAR insights make the compound a valuable tool for medicinal chemistry optimization studies.

8. Handling & Storage

Storage Conditions: Store in tightly sealed containers under dry, cool, and well-ventilated conditions. The compound is moisture-sensitive and should be protected from humidity, excessive heat, and direct sunlight. It decomposes upon contact with water.

Physicochemical Properties: Boiling point: 148 °C at 60 mmHg (lit.); Density: 1.372 g/mL at 25 °C (lit.); Refractive index: n20/D 1.544 (lit.); Flash point: 94 °C (201.2 °F); LogP: 4.05.

Purity Specifications: Commercial grades are available with purity ≥97-99%. The product is classified as a pharmaceutical intermediate and organic building block.

Safety Information: The compound is corrosive and causes severe skin burns and eye damage (H314). It can cause respiratory irritation upon inhalation and may be corrosive upon contact with skin or eyes. Appropriate personal protective equipment (gloves, protective clothing, eye/face protection) should be used during handling.

Intended Use: This product is intended strictly for laboratory research, drug discovery, and chemical synthesis applications. It is not intended for therapeutic, diagnostic, food, or household applications without appropriate regulatory approval.

Summary

The value of TRANS-3-(TRIFLUOROMETHYL)CINNAMOYL CHLORIDE (CAS: 64379-91-5) lies in its highly reactive acyl chloride functionality combined with the unique electronic and lipophilic properties imparted by the trifluoromethyl group. Its applications span organic synthesis (as an intermediate for amides, esters, and thioesters), pharmaceutical research (as a building block for drug discovery and enzyme inhibitor development), anticancer research, antioxidant studies, organic photoelectric materials (OLEDs and photovoltaics), pesticide synthesis, and structure-activity relationship studies. As a versatile acylating agent and pharmaceutical intermediate, this compound is an indispensable reagent for medicinal chemistry, materials science, and chemical synthesis research.