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  Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon Song Phys. Chem. Chem. Phys., 2014,16, 5295-5300
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  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043
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  Bidou Wang,Xifeng Chen Analyst, 2014,139, 5695-5699
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Professional Introduction to 3-chloro-6-methylpyridine-2-carbaldehyde (CAS No. 1060810-01-6)

3-chloro-6-methylpyridine-2-carbaldehyde, identified by the Chemical Abstracts Service Number (CAS No.) 1060810-01-6, is a significant intermediate in the field of organic synthesis and pharmaceutical development. This compound, featuring a chlorinated pyridine core with a formyl group at the 2-position and a methyl substituent at the 6-position, exhibits unique reactivity that makes it valuable for constructing complex molecular frameworks. Its structural attributes have garnered attention in recent years due to its utility in synthesizing bioactive molecules, particularly in medicinal chemistry.

The 3-chloro-6-methylpyridine-2-carbaldehyde scaffold provides a versatile platform for further functionalization, enabling chemists to explore diverse chemical transformations. The presence of the aldehyde group (–CHO) at the 2-position allows for condensation reactions with various nucleophiles, such as amines and hydrazines, yielding imines or hydrazones. These derivatives are often explored for their pharmacological properties. Additionally, the chloro substituent at the 3-position enhances electrophilic aromatic substitution reactions, facilitating further derivatization into heterocyclic systems.

In recent years, there has been growing interest in 3-chloro-6-methylpyridine-2-carbaldehyde due to its role in developing novel therapeutic agents. For instance, researchers have leveraged this compound to synthesize kinase inhibitors, which are crucial in targeting cancer and inflammatory diseases. The pyridine core is a common motif in many approved drugs, and modifications at the 2-, 3-, and 6-positions can fine-tune biological activity. A notable study published in 2022 demonstrated that derivatives of 3-chloro-6-methylpyridine-2-carbaldehyde exhibit potent inhibitory effects on specific protein kinases by modulating their active sites through hydrogen bonding and hydrophobic interactions.

The methyl group at the 6-position plays a critical role in determining the electronic properties of the pyridine ring. This substitution can influence both the reactivity of the aldehyde group and the overall solubility of the compound, making it adaptable for various drug delivery systems. Furthermore, computational studies have shown that the electronic distribution around the ring can be fine-tuned by this methyl group, allowing for precise control over interactions with biological targets.

Another area where 3-chloro-6-methylpyridine-2-carbaldehyde has shown promise is in the synthesis of antimicrobial agents. The combination of chloro and aldehyde functionalities makes it an excellent precursor for creating molecules that disrupt bacterial cell wall synthesis or interfere with essential metabolic pathways. Recent research has highlighted its utility in generating novel quinolone analogs, which exhibit broad-spectrum antimicrobial activity against resistant strains of bacteria. These findings underscore the importance of this compound as a building block in addressing emerging infectious diseases.

The versatility of 3-chloro-6-methylpyridine-2-carbaldehyde extends to materials science as well. Its ability to undergo cross-coupling reactions with boronic acids or halides allows for the construction of more complex organic frameworks, including polymers and liquid crystals. These materials have potential applications in electronics, optoelectronics, and advanced coatings. The ability to introduce specific functional groups via palladium-catalyzed reactions makes this compound a valuable asset in designing high-performance materials with tailored properties.

From a synthetic chemistry perspective, 3-chloro-6-methylpyridine-2-carbaldehyde offers several advantages as an intermediate. Its relatively stable structure allows for straightforward handling under mild conditions, reducing the risk of decomposition during reaction processes. Additionally, modern catalytic methods have enabled more efficient transformations, minimizing byproduct formation and improving yield. These advancements make it an attractive choice for industrial-scale synthesis where cost-effectiveness and scalability are paramount.

The pharmacokinetic properties of derivatives derived from 3-chloro-6-methylpyridine-2-carbaldehyde have also been extensively studied. Researchers have focused on optimizing bioavailability by modifying solubility and metabolic stability through appropriate functionalization strategies. For example, incorporating hydrophilic groups such as carboxylic acids or amides can enhance water solubility while preserving biological activity. Conversely, lipophilic substitutions can improve membrane permeability for better absorption into systemic circulation.

In conclusion,3-chloro-6-methylpyridine-2-carbaldehyde (CAS No. 1060810-01-6) is a multifaceted compound with broad applications across pharmaceuticals, materials science, and organic synthesis. Its unique structural features provide chemists with a powerful tool for designing novel molecules with tailored properties. As research continues to uncover new methodologies for functionalization and application development,this compound will undoubtedly remain relevant in advancing scientific discovery across multiple disciplines.

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