231291-22-8 | 6-(Trifluoromethyl)nicotinic acid

CAS:231291-22-8 | 6-(Trifluoromethyl)nicotinic acid,Description

6-Trifluoromethylnicotinic acid is a white powder. It is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis Analysis

Trifluoromethylpyridines, including 6-(Trifluoromethyl)nicotinic acid, are key structural motifs in active agrochemical and pharmaceutical ingredients. They are synthesized and applied in the agrochemical and pharmaceutical industries. More than 20 new trifluoromethylpyridine-containing agrochemicals have acquired ISO common names.

Molecular Structure Analysis

The molecular formula of 6-(Trifluoromethyl)nicotinic acid is C7H4F3NO2.

Chemical Reactions Analysis

6-(Trifluoromethyl)nicotinic acid is involved in various chemical reactions. For instance, it is used in the synthesis of trifluoromethylpyridines, which are key structural motifs in active agrochemical and pharmaceutical ingredients.

Physical And Chemical Properties Analysis

6-Trifluoromethylnicotinic acid is a white powder with a melting point of 193-197 °C. It has a boiling point of 259.3℃ at 760 mmHg. Its density is 1.484 g/cm3. Its flash point, refractive index and vapor pressure are 110.6℃, 1.475 and 0.007mmHg at 25°C, respectively.

Scientific Research Applications

Synthesis and Industrial Applications

The development of safe and economical synthesis methods for derivatives of 6-(trifluoromethyl)nicotinic acid has been a significant focus, particularly as intermediates in the creation of novel anti-infective agents. A noteworthy process involves trifluoromethylation utilizing an affordable system, highlighting the compound's role in synthesizing biologically active molecules (Mulder et al., 2013).

Chemical Synthesis and Characterization

Another aspect of research delves into the regioselective cross-coupling reactions of 6-(trifluoromethyl)nicotinic acid derivatives, demonstrating the carboxylic acid anion moiety's utility as a tunable directing group. This approach facilitates the selective synthesis of substituted nicotinic acids, contributing to diverse applications in chemical synthesis (Houpis et al., 2010).

Antioxidant and Vasorelaxant Properties

Research into thionicotinic acid derivatives has shown these compounds' potential as novel antioxidants and vasorelaxants. They exhibit dose-dependent maximal vasorelaxation and significant antioxidant activity, suggesting therapeutic potential for cardiovascular diseases (Prachayasittikul et al., 2010).

Anti-inflammatory and Atherosclerosis Prevention

A significant discovery is the anti-inflammatory effects of nicotinic acid and its receptor GPR109A in atherosclerosis prevention. It's shown that nicotinic acid can reduce atherosclerosis progression independently of its lipid-modifying effects through GPR109A activation on immune cells, suggesting a novel approach to treating cardiovascular diseases (Lukasova et al., 2011).

Herbicidal Applications

Furthermore, the synthesis of N-(arylmethoxy)-2-chloronicotinamides from nicotinic acid demonstrated excellent herbicidal activity against certain plants, highlighting potential applications in agricultural chemistry (Yu et al., 2021).

Pharmaceutical and Medicinal Chemistry

In the realm of medicinal chemistry , nicotinic acid analogs are explored for their inhibitory activity against carbonic anhydrase III, a target for managing dyslipidemia and cancer progression. This underscores the versatility of 6-(trifluoromethyl)nicotinic acid derivatives in developing new therapeutic agents (Mohammad et al., 2017).

Safety And Hazards

When handling 6-(Trifluoromethyl)nicotinic acid, personal protective equipment/face protection should be worn. Adequate ventilation should be ensured. It should not get in eyes, on skin, or on clothing. Ingestion and inhalation should be avoided. Dust formation should be avoided. Containers should be kept tightly closed in a dry, cool and well-ventilated place.

Future Directions

The use of 6-(Trifluoromethyl)nicotinic acid and its derivatives in the agrochemical and pharmaceutical industries is expected to continue to grow. For instance, compounds developed on the 2-amino-6-(trifluoromethyl)nicotinic acid scaffold have shown promise as RNase H dual inhibitors, indicating potential future directions for research and development.

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