402-66-4 | 5-Fluoronicotinic acid

CAS:402-66-4 | 5-Fluoronicotinic acid,Description

5-Fluoronicotinic acid is a chemical compound that has been explored for its diverse applications in the field of organic chemistry and materials science. Its molecular structure and properties enable it to serve as a precursor or building block for various chemical reactions and synthesis processes.

Synthesis Analysis

The synthesis of 5-Fluoronicotinic acid and its derivatives has been a subject of interest due to their potential applications. A notable method involves the facile room temperature synthesis of fluorine-18 labeled fluoronicotinic acid-2,3,5,6-tetrafluorophenyl ester, which does not require azeotropic drying of fluorine-18, presenting an efficient approach with over 75% conversion observed in just 5 minutes (Basuli et al., 2016). Another practical synthesis method described involves a palladium-catalyzed cyanation/reduction sequence for producing a key pharmaceutical intermediate (Wang et al., 2006).

Molecular Structure Analysis

The molecular structure of 5-Fluoronicotinic acid and its coordination compounds have been extensively studied, revealing a variety of structural configurations when combined with different metals. These structures range from intricate 3D metal–organic frameworks (MOFs) to simpler monomeric forms, demonstrating the versatility of 5-Fluoronicotinic acid in forming topologically diverse networks (Cui et al., 2015).

Chemical Reactions and Properties

5-Fluoronicotinic acid participates in various chemical reactions, leading to the formation of coordination compounds with interesting properties. For instance, its reaction with transition metals has been shown to yield compounds with potential applications in magnetism and luminescence (Cui et al., 2016).

Physical Properties Analysis

The physical properties of 5-Fluoronicotinic acid derivatives, such as solubility, melting points, and crystalline structures, are crucial for their application in material science. The luminescence properties of lanthanide(III) compounds derived from 5-Fluoronicotinic acid, for example, have been investigated, highlighting their potential as luminescent materials (Cui et al., 2016).

Scientific Research Applications

• Alkaloid Formation in Plants : 5-Fluoronicotinic acid was found to be involved in the formation of 5-fluoronicotine in Nicotiana tabacum plants. This indicates its role in the biosynthesis of specific alkaloids when introduced into plant systems (Leete, Bodem, & Manuel, 1971).
• Bacterial Inhibition : Streightoff (1963) discovered that 5-Fluoronicotinic acid and its analogues can inhibit various bacteria, including Streptococcus sp., Staphylococcus aureus, Escherichia coli, and Lactobacillus plantarum. This suggests its potential use as an antibacterial agent (Streightoff, 1963).
• Chemical Analysis : The paper by Hu Bao-xiang (2005) focuses on the separation and determination of 5-Fluoronicotinic acid and its esters, indicating its importance in analytical chemistry for precise measurement and separation techniques (Hu Bao-xiang, 2005).
• Medical Application : A study by Rowe et al. (1973) explored the use of a nicotinic-acid analogue metabolised as 5-Fluoronicotinic acid for lowering plasma-free-fatty-acids in cases of acute myocardial infarction, indicating its potential therapeutic application in cardiovascular conditions (Rowe, Dolder, Kirby, & Oliver, 1973).
• Synthesis of Derivatives : Zhou Yan-feng (2007) described the synthesis of ethyl 2,6-dichloro-5-fluoronicotinoyl acetate from 2,6-dichloro-5-fluoronicotinic acid, highlighting the compound's role in the synthesis of other chemical derivatives (Zhou Yan-feng, 2007).
• Pharmaceutical Intermediate Synthesis : Wang et al. (2006) presented a practical synthesis method for a key pharmaceutical intermediate involving 5-Fluoronicotinic acid, demonstrating its importance in the pharmaceutical industry (Wang et al., 2006).
• Cancer Treatment : Longley, Harkin, & Johnston (2003) discussed 5-Fluorouracil, which is structurally related to 5-Fluoronicotinic acid, and its mechanisms of action in cancer treatment. This indicates potential research interest in structurally similar compounds like 5-Fluoronicotinic acid for oncological applications (Longley, Harkin, & Johnston, 2003).

Safety And Hazards

5-Fluoronicotinic acid is considered hazardous. It causes skin irritation, serious eye irritation, and may cause respiratory irritation . It is recommended to avoid breathing its dust/fume/gas/mist/vapors/spray and to use it only outdoors or in a well-ventilated area .

Future Directions

5-Fluoronicotinic acid is a versatile building block in the generation of topologically diverse metal–organic and supramolecular networks . It can be used to prepare pesticides, daily chemicals, and animal husbandry food additives . In organic synthesis and transformation, the carboxyl group in the structure can be reduced to a hydroxyl group by lithium tetrahydroaluminum, and the carboxyl group can also be converted into an ester group or amide group .

More Information