Cas no 1805517-02-5 (2-Bromomethyl-4-chloro-6-methoxypyridine)
2-Bromomethyl-4-chloro-6-methoxypyridine Chemical and Physical Properties
Names and Identifiers
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- 2-Bromomethyl-4-chloro-6-methoxypyridine
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- Inchi: 1S/C7H7BrClNO/c1-11-7-3-5(9)2-6(4-8)10-7/h2-3H,4H2,1H3
- InChI Key: QRDMVIBARCOOLE-UHFFFAOYSA-N
- SMILES: BrCC1C=C(C=C(N=1)OC)Cl
Computed Properties
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 2
- Heavy Atom Count: 11
- Rotatable Bond Count: 2
- Complexity: 125
- XLogP3: 2.4
- Topological Polar Surface Area: 22.1
2-Bromomethyl-4-chloro-6-methoxypyridine Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Alichem | A029012132-250mg |
2-Bromomethyl-4-chloro-6-methoxypyridine |
1805517-02-5 | 95% | 250mg |
$940.80 | 2022-04-01 | |
| Alichem | A029012132-1g |
2-Bromomethyl-4-chloro-6-methoxypyridine |
1805517-02-5 | 95% | 1g |
$3,039.75 | 2022-04-01 |
2-Bromomethyl-4-chloro-6-methoxypyridine Related Literature
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Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161
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Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
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Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
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Yukiya Kitayama Polym. Chem., 2014,5, 2784-2792
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Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
Additional information on 2-Bromomethyl-4-chloro-6-methoxypyridine
Professional Introduction to 2-Bromomethyl-4-chloro-6-methoxypyridine (CAS No. 1805517-02-5)
2-Bromomethyl-4-chloro-6-methoxypyridine, identified by the Chemical Abstracts Service Number (CAS No.) 1805517-02-5, is a versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound belongs to the pyridine family, a class of nitrogen-containing heterocycles that are widely recognized for their broad spectrum of biological activities and utility in medicinal chemistry. The structural features of 2-Bromomethyl-4-chloro-6-methoxypyridine, including the presence of both bromomethyl and chloro substituents, make it an attractive intermediate for the synthesis of various pharmacologically active molecules.
The unique reactivity of 2-Bromomethyl-4-chloro-6-methoxypyridine stems from its dual functionalization at the 2-position (bromomethyl group) and 4-position (chloro group). The bromomethyl moiety is particularly noteworthy as it serves as a reactive handle for nucleophilic substitution reactions, enabling the introduction of diverse functional groups such as amines, alcohols, and thiols. This property has been exploited in the development of novel drug candidates targeting various therapeutic areas, including oncology, infectious diseases, and central nervous system disorders.
The chloro substituent at the 4-position further enhances the synthetic utility of this compound by allowing for cross-coupling reactions such as Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings. These reactions are fundamental in constructing complex molecular architectures, which are often required for achieving high binding affinity and selectivity in drug design. Recent advances in transition-metal-catalyzed cross-coupling techniques have further expanded the synthetic possibilities of 2-Bromomethyl-4-chloro-6-methoxypyridine, making it a valuable building block in modern medicinal chemistry.
In recent years, 2-Bromomethyl-4-chloro-6-methoxypyridine has been extensively studied for its potential applications in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and dysregulation of these pathways is implicated in numerous diseases, particularly cancer. By serving as a precursor for kinase inhibitors, this compound contributes to the ongoing effort to develop targeted therapies that modulate aberrant signaling networks. Several research groups have reported the use of 2-Bromomethyl-4-chloro-6-methoxypyridine in synthesizing novel kinase inhibitors with improved pharmacokinetic profiles and reduced off-target effects.
The methoxy group at the 6-position provides additional stability to the pyridine core while also serving as a potential site for further functionalization. This allows for the creation of more complex derivatives through etherification or hydrolysis reactions, broadening the scope of applications for 2-Bromomethyl-4-chloro-6-methoxypyridine. The compound's ability to undergo selective modifications at multiple sites makes it an indispensable tool in synthetic organic chemistry, particularly for those working on complex natural product analogs or drug candidates.
Another area where 2-Bromomethyl-4-chloro-6-methoxypyridine has shown promise is in the synthesis of agrochemicals. Pyridine derivatives are well-documented for their role as bioactive ingredients in pesticides and herbicides. The structural motifs present in 2-Bromomethyl-4-chloro-6-methoxypyridine make it a suitable candidate for developing new compounds that exhibit enhanced efficacy against plant pathogens while maintaining environmental safety. Researchers have leveraged its reactivity to design novel agrochemicals with improved selectivity and lower toxicity profiles.
The growing interest in green chemistry has also influenced the use of 2-Bromomethyl-4-chloro-6-methoxypyridine as a sustainable building block. Efforts have been made to develop synthetic routes that minimize waste and utilize environmentally benign conditions. For instance, catalytic methods that employ recyclable ligands or water as a solvent have been explored to enhance the sustainability of processes involving this compound. Such advancements align with global initiatives to promote sustainable pharmaceutical manufacturing practices.
Computational chemistry has played an increasingly important role in optimizing synthetic strategies involving 2-Bromomethyl-4-chloro-6-methoxypyridine. Molecular modeling techniques allow researchers to predict reaction outcomes and optimize reaction conditions before conducting experimental trials. This approach not only saves time but also reduces the consumption of resources by identifying the most efficient synthetic pathways. The integration of computational methods with traditional organic synthesis has accelerated progress in developing novel derivatives of this compound.
The future prospects for 2-Bromomethyl-4-chloro-6-methoxypyridine remain promising as new methodologies continue to emerge in chemical synthesis and drug discovery. Ongoing research is expected to uncover additional applications in areas such as material science and biotechnology, where its unique structural features offer distinct advantages. As our understanding of molecular interactions deepens, so too will our ability to harness the potential of this versatile intermediate.
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