• 1. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 2. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
• 3. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 4. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 5. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita

5-(Chloromethyl)-3-fluoro-2-methoxypyridine: A Comprehensive Overview

5-(Chloromethyl)-3-fluoro-2-methoxypyridine (CAS No. 1211535-18-0) is a versatile compound with significant applications in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique chloromethyl, fluoro, and methoxy substituents, has garnered attention for its potential in the development of novel drugs and therapeutic agents. This comprehensive overview aims to provide an in-depth understanding of the chemical properties, synthesis methods, and recent research advancements associated with 5-(chloromethyl)-3-fluoro-2-methoxypyridine.

The chemical structure of 5-(chloromethyl)-3-fluoro-2-methoxypyridine consists of a pyridine ring substituted with a chloromethyl group at the 5-position, a fluoro atom at the 3-position, and a methoxy group at the 2-position. These substituents contribute to the compound's unique electronic and steric properties, making it an attractive candidate for various chemical transformations and biological studies.

In terms of synthesis, 5-(chloromethyl)-3-fluoro-2-methoxypyridine can be prepared through several methods. One common approach involves the reaction of 2-methoxy-3-fluoropyridine with chloromethyl methyl ether (CMME) in the presence of a suitable catalyst. This method has been optimized to achieve high yields and purity, making it suitable for large-scale production. Another synthetic route involves the alkylation of 2-methoxy-3-fluoropyridine with chloromethyl tosylate, which has also shown promising results in terms of yield and selectivity.

The chloromethyl group in 5-(chloromethyl)-3-fluoro-2-methoxypyridine is particularly reactive and can undergo various chemical transformations such as nucleophilic substitution reactions. This reactivity makes it a valuable intermediate in the synthesis of more complex molecules, including pharmaceuticals and agrochemicals. Recent studies have explored the use of this compound as a building block for the synthesis of novel antiviral agents, where its chloromethyl group serves as a key functional handle for further derivatization.

The presence of the fluoro atom at the 3-position imparts significant electronic effects on the pyridine ring, influencing its reactivity and biological properties. Fluorination is known to enhance the lipophilicity and metabolic stability of organic compounds, making them more suitable for drug development. Research has shown that 5-(chloromethyl)-3-fluoro-2-methoxypyridine derivatives exhibit improved pharmacokinetic profiles compared to their non-fluorinated counterparts, which is crucial for optimizing drug efficacy and safety.

The methoxy group at the 2-position further modulates the electronic properties of the pyridine ring, contributing to its overall stability and reactivity. This substituent has been shown to enhance solubility and bioavailability, which are important factors in drug design. Studies have demonstrated that compounds containing this substituent pattern exhibit enhanced binding affinity to specific biological targets, such as enzymes and receptors.

In addition to its synthetic utility, 5-(chloromethyl)-3-fluoro-2-methoxypyridine has been investigated for its potential therapeutic applications. Recent research has focused on its use as an intermediate in the synthesis of drugs targeting neurological disorders, cancer, and infectious diseases. For instance, derivatives of this compound have shown promising activity against neurodegenerative diseases by modulating specific signaling pathways involved in neuronal survival and function.

The biological activity of 5-(chloromethyl)-3-fluoro-2-methoxypyridine derivatives has also been evaluated in preclinical studies. These studies have demonstrated that certain derivatives exhibit potent antitumor activity by inhibiting key enzymes involved in cancer cell proliferation and survival. Furthermore, some derivatives have shown antiviral activity against various pathogens, highlighting their potential as broad-spectrum antiviral agents.

To ensure the safe and effective use of 5-(chloromethyl)-3-fluoro-2-methoxypyridine, it is essential to conduct thorough toxicological evaluations. Preclinical studies have assessed the safety profile of this compound and its derivatives, providing valuable insights into their potential side effects and mechanisms of action. These studies have shown that while generally well-tolerated, certain derivatives may require further optimization to minimize adverse effects.

In conclusion, 5-(chloromethyl)-3-fluoro-2-methoxypyridine (CAS No. 1211535-18-0) is a highly versatile compound with significant potential in medicinal chemistry and pharmaceutical research. Its unique chemical structure and reactivity make it an attractive intermediate for the synthesis of novel drugs and therapeutic agents. Ongoing research continues to explore its applications in various fields, contributing to advancements in drug discovery and development.

• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)