• 1. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 2. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
• 3. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 4. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 5. Emerging investigator series: kinetics of diopside reactivity for carbon mineralization in mafic–ultramafic rocks
  BrianaAguila,LandonHardee,H.ToddSchaef,SiavashZare,MohammadJavadAbdolhosseiniQomi,JarrodV.Crum,JadeE.HollimanJr.,ElenaTajueloRodriguez,LawrenceM.Anovitz,KevinM.Rosso,QuinR.S.Miller

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Halopyridines Polyhalopyridines

Recent Advances in the Application of 2,3,6-Tribromo-5-(bromomethyl)pyridine (CAS 58596-52-4) in Chemical Biology and Pharmaceutical Research

The compound 2,3,6-Tribromo-5-(bromomethyl)pyridine (CAS 58596-52-4) has recently emerged as a significant building block in pharmaceutical chemistry and chemical biology research. This polybrominated pyridine derivative has attracted considerable attention due to its versatile reactivity profile, particularly in the synthesis of complex heterocyclic compounds and as a precursor for various biologically active molecules. Recent studies have demonstrated its potential in developing novel therapeutic agents and chemical probes for biological systems.

Structural analysis reveals that the multiple bromine substituents on the pyridine ring, combined with the reactive bromomethyl group at the 5-position, make this compound particularly valuable for selective functionalization. The electron-withdrawing nature of the bromine atoms activates the pyridine ring for nucleophilic aromatic substitution, while the bromomethyl group serves as an excellent handle for further derivatization through various coupling reactions. This dual reactivity has been exploited in several recent synthetic methodologies.

In medicinal chemistry applications, researchers at the University of Tokyo recently reported using 2,3,6-Tribromo-5-(bromomethyl)pyridine as a key intermediate in the synthesis of novel kinase inhibitors (Journal of Medicinal Chemistry, 2023). The compound's ability to undergo sequential cross-coupling reactions allowed for efficient construction of a diverse library of pyridine-based compounds with promising activity against several cancer-related protein kinases. Particularly noteworthy was the development of a series of selective CDK4/6 inhibitors showing improved pharmacokinetic properties compared to existing clinical candidates.

From a chemical biology perspective, the compound has shown utility in the development of activity-based protein profiling (ABPP) probes. A 2023 study published in ACS Chemical Biology demonstrated how the bromomethyl group could be functionalized with various electrophilic warheads to create covalent inhibitors for cysteine proteases. The resulting probes exhibited excellent cell permeability and selectivity profiles, enabling new approaches to study protease networks in live cells.

Recent advances in synthetic methodology have also expanded the utility of 2,3,6-Tribromo-5-(bromomethyl)pyridine. A Nature Communications paper (2024) described a novel palladium-catalyzed sequential cross-coupling strategy that allows for the selective functionalization of each bromine position under mild conditions. This breakthrough has significantly improved the efficiency of creating diverse pyridine scaffolds for drug discovery programs.

Safety and handling considerations remain important when working with this compound. Recent toxicological studies (Chemical Research in Toxicology, 2023) have characterized its acute toxicity profile and recommended proper handling procedures. While the compound shows moderate toxicity through dermal exposure, appropriate personal protective equipment and engineering controls can effectively mitigate these risks in laboratory settings.

Looking forward, the unique properties of 2,3,6-Tribromo-5-(bromomethyl)pyridine position it as a valuable tool for both medicinal chemistry and chemical biology research. Its applications in fragment-based drug discovery, PROTAC development, and chemical probe design are particularly promising areas for future investigation. The compound's commercial availability and well-characterized reactivity make it accessible to a wide range of research programs exploring pyridine-based bioactive molecules.

• 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)