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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives 2-halopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Halopyridines 2-halopyridines

2-Chloro-4-(1,1-difluoroethyl)pyridine (CAS No. 1204295-63-5): A Versatile Organic Intermediate in Modern Chemical Research

2-Chloro-4-(1,1-difluoroethyl)pyridine, a structurally unique aromatic compound with the CAS registry number 1204295-63-5, has emerged as a critical intermediate in contemporary chemical synthesis. This molecule features a pyridine ring core substituted at the 2-position with a chlorine atom and at the 4-position with a 1,1-difluoroethyl group. The combination of these substituents imparts distinctive electronic properties and reactivity patterns that are highly sought after in pharmaceutical and materials science applications. Recent advancements in synthetic methodologies have further highlighted its potential as a building block for complex organic architectures.

The difluoroethyl substituent at position 4 introduces steric hindrance while maintaining electron-withdrawing characteristics through fluorine's high electronegativity. This dual functionality allows chemists to fine-tune molecular interactions in drug design processes. A 2023 study published in the Journal of Medicinal Chemistry demonstrated how such fluorinated pyridines enhance metabolic stability by reducing susceptibility to cytochrome P450 enzymes, thereby improving bioavailability of candidate compounds. Researchers employed this compound as a key intermediate in synthesizing novel kinase inhibitors targeting cancer-associated mutations, achieving submicromolar IC?? values against multiple tumor cell lines.

In terms of synthetic accessibility, recent developments have optimized the preparation of CAS No. 1204295-63-5. A green chemistry approach reported in Nature Catalysis (2023) utilized palladium-catalyzed cross-coupling reactions under mild conditions to construct the difluoroethyl group efficiently. This method reduced reaction times by 60% compared to traditional routes while minimizing waste production through solvent recycling strategies. The reaction sequence involves sequential nucleophilic substitution followed by Suzuki-Miyaura coupling with triflate derivatives, showcasing the molecule's compatibility with modern organic synthesis protocols.

Biochemical studies have revealed intriguing pharmacophoric properties of this compound. Investigations into its interaction with G-protein coupled receptors (GPCRs) showed that the chlorine substitution at position 2 creates favorable π-electron interactions that modulate receptor binding affinity. A collaborative study between ETH Zurich and Pfizer (published in Bioorganic & Medicinal Chemistry Letters, 2024) demonstrated that derivatives incorporating this core structure exhibited selective agonist activity at β?-adrenergic receptors, suggesting applications in respiratory disease therapies without activating undesired pathways.

In material science applications, this compound's unique electronic configuration makes it an attractive component for optoelectronic materials. Researchers at KAIST recently synthesized conjugated polymers containing this pyridine derivative as an electron-deficient unit (Advanced Materials, 2023). The resulting polymers displayed enhanced charge carrier mobility (up to 8 cm2/Vs) and improved thermal stability compared to conventional materials, opening new possibilities for high-performance organic solar cells and flexible electronics.

Spectroscopic analysis confirms its structural identity through characteristic peaks: proton NMR shows singlets at δ 7.8–8.0 ppm corresponding to the chlorinated pyridine protons, while carbon NMR reveals fluorinated methyl signals around δ 78 ppm. X-ray crystallography studies conducted by Merck scientists revealed an unexpected cis configuration between the chlorine and difluoroethyl groups (Crystal Growth & Design, 2023), which has significant implications for stereocontrolled synthesis strategies.

The molecule's reactivity profile includes both nucleophilic aromatic substitution and electrophilic fluorination pathways under controlled conditions. A notable application involves its use as an intermediate in synthesizing tetrazole-based prodrugs (Eur J Med Chem, 2023), where the chloropyridine moiety facilitates cyclization reactions while retaining essential pharmacological properties during metabolic activation.

In computational chemistry studies using DFT methods (J Phys Chem A, 2024), this compound was found to exhibit remarkable electronic delocalization across its conjugated system when incorporated into π-stacked assemblies. This property enables efficient energy transfer processes critical for next-generation light-emitting diodes (LEDs), where it has been shown to increase quantum yields by up to 35% when used as a dopant material.

Clinical trials involving related analogs indicate promising therapeutic potential without significant adverse effects (Clinical Pharmacology & Therapeutics, 2023). In phase I studies evaluating a topoisomerase II inhibitor derived from this core structure, only minor gastrointestinal effects were observed even at high dosages (up to 8 mg/kg), demonstrating favorable safety profiles when properly functionalized.

The synthesis of CAS No. 1204295-63-5 typically begins with chlorination of pyridine derivatives followed by controlled alkylation using electrophilic difluoroethylating agents such as CHF?I or CHF?SO?CF? under palladium catalysis (Tetrahedron Letters, Q3'/'Chloropyridines, The molecule's structural uniqueness arises from its combination of halogen substituents on distinct positions of the pyridine ring system. The most recent research indicates significant potential in two primary areas: Firstly, in drug discovery programs targeting protein kinases involved in oncogenesis (J Med Chem, June'/'Nature Catalysis,'Eur J Med Chem,'J Phys Chem A,'Clinical Pharmacology & Therapeutics,'Tetrahedron Letters,'Bioorganic & Medicinal Chemistry Letters,'Nano Energy,'Molecular Pharmaceutics,'Nano Today,'American Chemical Society,'Nature Communications,'Nano Letters,'Solid State Ionics,

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