99199-60-7 | 6-Fluorochromane-2-carboxylic acid

CAS:99199-60-7 | 6-Fluorochromane-2-carboxylic acid,Description

Synthesis Analysis

The synthesis of 6-Fluorochromane-2-carboxylic acid involves several steps, starting from p-fluorophenol. Yang et al. (2005) describe the synthesis of 6-fluoro-4-chromanone-2-carboxylic acid and 6-fluorochroman-2-carboxylic acid, further obtaining the (R)- and (S)-6-fluorochroman-2-carboxylic acids by forming salts with optically active amines (Yang et al., 2005). Another synthesis pathway, presented by Ning (2007), involves methylization, Friedel-Crafts reaction, and Michael addition, resulting in a yield of 78% (Ning, 2007).

Molecular Structure Analysis

Barili et al. (2001) conducted a detailed study on the molecular structure of a related compound, 6-fluoro-7-chloro-4-oxo-4H-chromene 3-carboxylic acid, using NMR spectroscopy and X-ray crystallography (Barili et al., 2001). This study provides insights into the molecular geometry and electronic structure of fluorochromane derivatives.

Chemical Reactions and Properties

The chemical reactions of 6-Fluorochromane-2-carboxylic acid include its interaction with other compounds to form novel derivatives. Kumar et al. (2006) reported the synthesis of novel benzimidazoles by condensing 6-fluoro-3,4-dihydro-2H-chroman-2-carboxylic acid with various electrophiles (Kumar et al., 2006).

Physical Properties Analysis

The physical properties, such as solubility, melting point, and crystal structure, can be inferred from studies on similar fluorinated compounds. For instance, the research by Møllendal et al. (2005) on 1-fluorocyclopropanecarboxylic acid provides information on the conformational properties and intramolecular hydrogen bonding, which are relevant to understanding the physical characteristics of fluorinated carboxylic acids (Møllendal et al., 2005) .

Chemical Properties Analysis

The chemical properties of 6-Fluorochromane-2-carboxylic acid can be deduced from its reactivity in synthesis reactions and its interactions with other chemical agents. The study by Tajbakhsh et al. (2005) describes the use of fluorochromates in oxidative deprotection reactions, shedding light on the reactivity of fluorinated compounds (Tajbakhsh et al., 2005).

Scientific Research Applications

• Oxidative Deprotection in Organic Synthesis : 2,6-Dicarboxypyridinium fluorochromate is utilized for the oxidative deprotection of oximes, phenylhydrazones, and semicarbazones into their carbonyl analogues under solvent-free conditions, indicating its potential in organic synthesis (Tajbakhsh et al., 2005)(source).
• Synthesis of Aryl Triazoles and Thiazolidinones : The efficient and facile synthesis of 1,2,4-aryl triazoles and 4-thiazolidinones bearing a 6-fluorochroman nucleus has been demonstrated, showing potential applications in organic synthesis and catalysis (Vekariya et al., 2014)(source).
• Pharmaceutical Applications : A study on novel 2-(6-fluorochroman-2-yl)-1-alkyl/acyl/aroyl-1H-benzimidazoles revealed promising antibacterial activity against Salmonella typhimurium, suggesting potential pharmaceutical applications (Kumar et al., 2006)(source).
• Environmental Studies : The biodegradation of 6:2 fluorotelomer alcohol in surface sediment significantly alters bacterial community structure, indicating environmental implications (Wang et al., 2017)(source).
• Synthesis and Resolution Research : The successful synthesis and resolution of (R)- and (S)-6-fluorochroman-2-carboxylic acids from p-fluorophenol have been achieved, important for chiral compound research (Yang et al., 2005)(source).
• Degradation in Advanced Oxidation Processes : 6:2 fluorotelomer sulfonate potassium salt (6:2 FTS-K) shows promise as a more degradable alternative to PFOS in the hard chrome electroplating industry, with implications for environmental remediation (Yang et al., 2014)(source).
• Optical Applications : The synthesis of optically active 2-methylchroman derivatives and their application as chiral dopants for nematic liquid crystals has been explored, showing potential in optical technologies (Shitara et al., 2000)(source).

Safety And Hazards

For safety and hazards, it is recommended to avoid contact with skin and eyes, avoid formation of dust and aerosols, and obtain special instructions before use. Appropriate exhaust ventilation should be provided at places where dust is formed.

Future Directions

The future directions for 6-Fluorochromane-2-carboxylic acid involve improving the production process. Currently, the production of (S) and ®-FCCAs mainly depends on chemical resolution, which is a complex, low yield, and highly polluting process. Therefore, there is a need for more efficient and environmentally friendly production methods.

More Information