189281-66-1 | METHYL 2,6-DICHLORO-5-FLUORONICOTINATE

CAS:189281-66-1 | METHYL 2,6-DICHLORO-5-FLUORONICOTINATE,Description

Synthesis Analysis

The synthesis of Methyl 2,6-dichloro-5-fluoronicotinate involves several key steps, including the regioselective chlorination of precursor molecules, palladium-catalyzed cyanation, and reduction sequences. A notable method includes the highly selective monodechlorination of 2,6-dichloro-5-fluoronicotinic acid to afford the desired nicotinic acid derivatives (Wang et al., 2006). Additionally, a practical approach for synthesizing derivatives through substitution and hydrolysis has been established, yielding significant intermediates for anticancer drugs (Zhang et al., 2019).

Molecular Structure Analysis

The molecular structure of derivatives related to Methyl 2,6-dichloro-5-fluoronicotinate has been elucidated through various spectroscopic and X-ray crystallography techniques. For instance, the structure of ethyl 2,6-dichloro-5-fluoronicotinoyl acetate, a closely related compound, has been confirmed through NMR and MS spectrum analysis, revealing important insights into the compound's configuration and electronic environment (Yao et al., 2013).

Chemical Reactions and Properties

Methyl 2,6-dichloro-5-fluoronicotinate participates in various chemical reactions, including decarboxylative couplings and electrophilic substitutions, which are pivotal for the synthesis of fluorinated organic compounds. The compound's reactivity is significantly influenced by its halogen substituents, facilitating the development of novel synthetic methodologies (Lee et al., 2007).

Scientific Research Applications

Fluorescent Chemosensors

• Application : 4-Methyl-2,6-diformylphenol (DFP) serves as a key platform for developing chemosensors capable of detecting various analytes, including metal ions, anions, and neutral molecules. The high selectivity and sensitivity of DFP-based chemosensors have been extensively documented, highlighting their potential in chemical detection and analysis (Roy, 2021).

Fluorescent Dye Applications

• Clinical and Surgical Use : Methylene blue, a fluorescent dye, has found applications beyond its traditional use, especially in intraoperative fluorescent imaging. This highlights the utility of fluorescent compounds in medical and surgical settings, offering insights into their potential applications in enhancing surgical techniques and cancer detection (Cwalinski et al., 2020) .

Fluorinated Compounds in Cancer Treatment

• Cancer Therapy : The review on fluorinated pyrimidines, particularly 5-Fluorouracil (5-FU), emphasizes their significant role in cancer treatment. The study delves into the synthesis, metabolism, and the evolving understanding of their mechanisms, including their effects on DNA and RNA, which could be relevant to the pharmacological applications of related fluorinated compounds (Gmeiner, 2020).

Synthesis and Manufacturing

• Chemical Synthesis : The practical synthesis of 2-Fluoro-4-bromobiphenyl, a key intermediate in the manufacture of certain pharmaceuticals, showcases the methodologies and challenges in synthesizing fluorinated compounds, which might share similarities with the synthesis of Methyl 2,6-dichloro-5-fluoronicotinate (Qiu et al., 2009).

Safety And Hazards

“Methyl 2,6-dichloro-5-fluoronicotinate” 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 avoid contact with skin and eyes, avoid formation of dust and aerosols, and provide appropriate exhaust ventilation at places where dust is formed.

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