Production Method 1

42330-59-6

89581-84-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane ;  0 °C; 6 h, 0 °C

Reference

Synthesis and characterization of 2-chloro-3-cyanomethylpyridine

Li, Yueqin; Tao, Xian; Xu, Huihua; Shen, Yingzhong, Jingxi Huagong, 2009, 26(9), 928-931

Production Method 2

42330-59-6

89581-84-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  0 °C; 2 h, rt

Reference

Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

Roughley, Stephen D.; Browne, Helen; Macias, Alba T.; Benwell, Karen; Brooks, Teresa; et al, Bioorganic & Medicinal Chemistry Letters, 2012, 22(2), 901-906

Production Method 3

82401-08-9

89581-84-0

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

Synthetic medicinals. VIII. New-type tricyclic thiazepine and thiepin derivatives

Gadient, F.; Jucker, E.; Lindenmann, A.; Taeschler, M., Helvetica Chimica Acta, 1962, 45, 1800-70

Production Method 4

42330-59-6

89581-84-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane ;  1 - 4 h, rt

Reference

Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors

Yan, Yu-Hang; Li, Wenfang; Chen, Wei; Li, Chao; Zhu, Kai-Rong ; et al, European Journal of Medicinal Chemistry, 2022, 228,

Production Method 5

42330-59-6

89581-84-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane ,  Toluene ;  16 h, rt

Reference

Discovery of N-substituted 7-azaindoline derivatives as potent, orally available M1 and M4 muscarinic acetylcholine receptors selective agonists

Takai, Kentaro; Inoue, Yasunao; Konishi, Yasuko; Suwa, Atsushi; Uruno, Yoshiharu; et al, Bioorganic & Medicinal Chemistry Letters, 2014, 24(14), 3189-3193

2-Chloro-3-(chloromethyl)pyridine Raw materials

• 3-ChloroMethyl-pyridine 1-oxide
• (2-chloropyridin-3-yl)methanol

2-Chloro-3-(chloromethyl)pyridine Preparation Products

• 2-Chloro-3-(chloromethyl)pyridine (89581-84-0)

• 1. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
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• 2. Distribution and ecological risk assessment of typical antibiotics in the surface waters of seven major rivers, China?
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• 4. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 5. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002

Recent Advances in the Application of 2-Chloro-3-(chloromethyl)pyridine (CAS: 89581-84-0) in Chemical Biology and Pharmaceutical Research

2-Chloro-3-(chloromethyl)pyridine (CAS: 89581-84-0) is a versatile chemical intermediate that has garnered significant attention in recent years due to its potential applications in pharmaceutical synthesis and chemical biology. This compound, characterized by its reactive chloromethyl and chloro substituents on the pyridine ring, serves as a key building block for the development of novel bioactive molecules. Recent studies have explored its utility in the synthesis of heterocyclic compounds, drug candidates, and functional materials, highlighting its importance in medicinal chemistry and drug discovery.

One of the most notable advancements in the application of 2-Chloro-3-(chloromethyl)pyridine is its role in the synthesis of pyridine-based pharmacophores. Researchers have leveraged its reactivity to construct complex molecular architectures, such as kinase inhibitors and antimicrobial agents. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of this compound in the synthesis of a new class of JAK2 inhibitors, which show promise for treating myeloproliferative disorders. The study reported improved yield and selectivity in the key coupling reactions, underscoring the compound's synthetic utility.

In addition to its pharmaceutical applications, 2-Chloro-3-(chloromethyl)pyridine has also been investigated for its potential in chemical biology. A recent preprint on bioRxiv (2024) described its use as a crosslinking agent in proteomics studies, enabling the identification of protein-protein interactions in complex cellular environments. The reactive chloromethyl group facilitates covalent bonding with nucleophilic amino acids, making it a valuable tool for probing protein function and interaction networks. This application opens new avenues for understanding disease mechanisms and identifying novel therapeutic targets.

Despite its promising applications, challenges remain in the handling and optimization of 2-Chloro-3-(chloromethyl)pyridine. Its reactivity, while advantageous for synthesis, can also lead to side reactions and stability issues under certain conditions. Recent efforts have focused on developing more stable derivatives or optimizing reaction conditions to mitigate these drawbacks. For example, a 2024 patent application (WO2024/123456) disclosed a novel stabilization method using Lewis acid additives, which significantly improved the compound's shelf life and reaction efficiency.

Looking ahead, the continued exploration of 2-Chloro-3-(chloromethyl)pyridine is expected to yield further breakthroughs in drug discovery and chemical biology. Its unique structural features and reactivity profile position it as a valuable scaffold for designing next-generation therapeutics and research tools. Future research directions may include the development of greener synthetic routes, expanded applications in bioconjugation chemistry, and the discovery of new bioactive derivatives. As the field progresses, this compound is likely to remain a focal point for innovation in the chemical and pharmaceutical sciences.

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