779-89-5 | 3-(Trifluoromethyl)cinnamic acid

CAS:779-89-5 | 3-(Trifluoromethyl)cinnamic acid,Description

Synthesis Analysis

The synthesis of 3-(Trifluoromethyl)cinnamic acid and its derivatives involves various methods, including copper-catalyzed decarboxylative trifluoroethylation of cinnamic acids, which showcases high functional group tolerance and excellent selectivity (Zhang et al., 2017). Another method involves the reaction of 4-aryl-6-(trifluoromethyl)-2H-pyran-2-ones with sodium azide, leading to highly functionalized CF3-1,2,3-triazoles (Usachev et al., 2011). These methods highlight the versatility and efficiency in synthesizing trifluoromethyl derivatives of cinnamic acid.

Molecular Structure Analysis

The crystal structure of trans-4-(trifluoromethyl) cinnamic acid has been determined, revealing significant insights into its molecular geometry and phase transitions at varying temperatures (Howard & Sparkes, 2008). This study contributes to a deeper understanding of the physical properties and stability of the compound under different conditions.

Chemical Reactions and Properties

Cinnamic acids undergo various chemical reactions, including superacid-catalyzed reactions and decarboxylative cyclizations, demonstrating the reactivity and versatility of these compounds (Rendy et al., 2004). The formation of dicationic intermediates and the ability to synthesize electron-deficient chalcones and heterocyclic chalcones are notable characteristics.

Physical Properties Analysis

The physical properties of 3-(Trifluoromethyl)cinnamic acid, including its phase behavior and crystal structure, have been extensively studied. Investigations into its polymorphic phase transformations provide valuable insights into the material's behavior under different thermal conditions (Ahn et al., 2001).

Chemical Properties Analysis

The chemical properties of 3-(Trifluoromethyl)cinnamic acid derivatives have been explored in various studies, highlighting their potential as intermediates in the synthesis of pharmaceuticals and agrochemicals due to the introduction of the trifluoromethyl group (Chu & Qing, 2014). These properties are crucial for enhancing chemical and metabolic stability, improving lipophilicity, and increasing protein bind affinity.

Scientific Research Applications

1. Treatment of Resistant Bacterial Infections

• Summary of Application: 3-(Trifluoromethyl)cinnamic acid is used in the synthesis of anilides, which are tested against reference strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 and resistant clinical isolates of methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (VRE). All the compounds were evaluated in vitro against Mycobacterium smegmatis ATCC 700084 and M. marinum CAMP 5644.
• Methods of Application: A series of thirty-two anilides of 3-(trifluoromethyl)cinnamic acid was prepared by microwave-assisted synthesis.
• Results or Outcomes: Some of the synthesized anilides showed antistaphylococcal (MICs/MBCs 0.15–5.57 µM) as well as anti-enterococcal (MICs/MBCs 2.34–44.5 µM) activity.

2. Synthesis of Cinacalcet

• Summary of Application: 3-(Trifluoromethyl)cinnamic acid is used in the synthesis of cinacalcet.
• Methods of Application: The specific methods of application or experimental procedures are not provided in the source.
• Results or Outcomes: The specific results or outcomes are not provided in the source.

3. Hydrophobic Probe

• Summary of Application: trans-3,5-Bis(trifluoromethyl)cinnamic acid (F-CIN), a derivative of 3-(Trifluoromethyl)cinnamic acid, is used as a hydrophobic probe to investigate the interactions between hydrophobic guest molecules and polymers forming the micelle core.
• Methods of Application: The specific methods of application or experimental procedures are not provided in the source.
• Results or Outcomes: The specific results or outcomes are not provided in the source.

4. Synthesis of Cinacalcet

• Summary of Application: 3-(Trifluoromethyl)cinnamic acid is used in the synthesis of cinacalcet, a drug for the control and treatment of secondary hyperparathyroidism (in the dialysis population), primary hyperparathyroidism where the patient may not be a candidate for surgical treatment, and for the treatment of calciphylaxis in patients with end-stage renal disease or in patients on dialysis.
• Methods of Application: The specific methods of application or experimental procedures are not provided in the source.
• Results or Outcomes: The specific results or outcomes are not provided in the source.

5. Antimicrobial Screening

• Summary of Application: A series of anilides of 3-(trifluoromethyl)cinnamic acid was prepared and subjected to extensive antimicrobial screening against Gram-positive bacteria and two mycobacterial strains.
• Methods of Application: The specific methods of application or experimental procedures are not provided in the source.
• Results or Outcomes: Some of the synthesized anilides showed antistaphylococcal (MICs/MBCs 0.15–5.57 µM) as well as anti-enterococcal (MICs/MBCs 2.34–44.5 µM) activity.

6. Hydrophobic Probe

• Summary of Application: trans-3,5-Bis(trifluoromethyl)cinnamic acid (F-CIN), a derivative of 3-(Trifluoromethyl)cinnamic acid, was employed as a hydrophobic probe to investigate the interactions between hydrophobic guest molecules and polymers forming the micelle core.
• Methods of Application: The specific methods of application or experimental procedures are not provided in the source.
• Results or Outcomes: The specific results or outcomes are not provided in the source.

Safety And Hazards

3-(Trifluoromethyl)cinnamic acid is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to wear personal protective equipment/face protection, ensure adequate ventilation, avoid getting in eyes, on skin, or on clothing, avoid ingestion and inhalation, and avoid dust formation.

Future Directions

The use of cinnamic acid provides an approach to the research and development of biobased plastics for the reduction of global warming caused by the increasing amounts of carbon dioxide in the atmosphere. Cinnamic acids in the metabolic systems of plants and microorganisms have been extensively studied. These cinnamates are reactive to ultraviolet (UV) light, and polymers based on these acids exhibit unique properties.

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