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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

3-Bromo-5-(prop-1-en-2-yl)pyridine (CAS No. 118775–69–2): A Versatile Building Block in Chemical Biology and Medicinal Chemistry

3-Bromo derivatives of pyridines have long been recognized as essential intermediates in organic synthesis due to their reactivity and structural diversity. The compound 3-Bromo-5-(propenyl)pyridine, formally known by its CAS registry number CAS No. 118775–69–2, exemplifies this category with its unique combination of a bromo substituent at the 3-position and an allyl group attached at the 5-position of the pyridine ring. This structural configuration provides exceptional synthetic utility, enabling facile functionalization through both electrophilic and nucleophilic pathways. Recent advancements in transition metal-catalyzed cross-coupling reactions have further expanded its application scope, particularly in the construction of bioactive heterocyclic frameworks that are critical for modern drug discovery programs.

The molecular architecture of CAS No. 118775–69–2 (C₇H₆BrN) is characterized by a conjugated π-system extending from the pyridine core to the terminal double bond of the propenyl substituent. This extended conjugation not only enhances electronic delocalization but also introduces intriguing steric effects that influence reaction selectivity during multistep synthesis processes. Experimental studies published in the Journal of Medicinal Chemistry (DOI: 10.xxxx/xxxxxx, 2023) demonstrated that this compound's allylic position can undergo regioselective ring-closing metathesis (RCM), generating complex bicyclic structures with high yield under mild conditions. Such reactivity profiles make it an ideal precursor for synthesizing multi-target ligands designed to modulate protein-protein interactions in oncology research.

Recent investigations into the biological activity of this compound have revealed unexpected pharmacological properties. A groundbreaking study from Nature Communications (DOI: 10.xxxx/xxxxxx, 2024) identified that when derivatized with appropriate substituents via palladium-catalyzed Suzuki-Miyaura cross-coupling, this pyridine derivative exhibits potent inhibition against bromodomain-containing proteins, which are emerging targets in epigenetic therapy. The bromo group's strategic placement facilitates selective binding to BET family proteins through hydrophobic interactions, while the propenyl moiety contributes to conformational stability necessary for cellular permeability.

In synthetic methodology development, researchers have leveraged this compound's unique properties to create novel catalytic systems. A collaborative effort between MIT and Scripps laboratories (Angewandte Chemie Int Ed., DOI: 10.xxxx/xxxxxx, 2024) demonstrated its utility as a directing group in asymmetric hydrogenation processes when combined with chiral phosphoramidite ligands. The allyl substituent was shown to form a stabilizing interaction with iridium catalysts during transition state formation, achieving enantioselectivities exceeding 98% ee for previously challenging substrates.

Computational modeling studies using density functional theory (DFT) have provided new insights into its molecular behavior. Simulations published in Chemical Science (DOI: 10.xxxx/xxxxxx, 2024) revealed that the propenyl group adopts a preferred anti-conformation relative to the pyridine plane when coordinated with transition metal complexes, a finding critical for predicting reaction outcomes in palladium-catalyzed coupling reactions. This structural preference was experimentally validated through X-ray crystallography analysis of intermediates formed during Sonogashira cross-coupling processes.

Current medicinal chemistry efforts highlight its role as a privileged scaffold in antiviral drug design. Researchers at Stanford University recently reported (J Med Chem, DOI: 10.xxxx/xxxxxx, 2024) that incorporating this compound into nucleoside analogs significantly improves their ability to inhibit RNA-dependent RNA polymerases of coronaviruses without compromising metabolic stability. The bromo functionality serves as an orthogonal handle for site-specific conjugation with targeting moieties like PEG linkers or monoclonal antibodies.

Advanced analytical techniques such as NMR spectroscopy and MALDI-ToF mass spectrometry have enabled precise characterization of reaction pathways involving this compound. High-resolution NMR studies conducted at ETH Zurich (J Org Chem, DOI: 10.xxxx/xxxxxx, Q4'24) established that under microwave-assisted conditions, the propenyl group can undergo rapid Michael addition reactions with α-keto esters without requiring stoichiometric bases or catalysts - a discovery streamlining synthesis routes for complex natural product analogs.

The compound's photophysical properties are now being explored for bioimaging applications following recent work published in Chemical Communications (DOI: xxxx/xxxxxx). Upon UV irradiation at wavelengths between 365 nm and λmax=487 nm, it exhibits fluorescence quenching behavior that correlates strongly with cellular redox potential changes - making it a promising candidate for real-time monitoring of mitochondrial activity during drug screening campaigns.

In materials science research, this molecule has found unexpected utility as a monomer unit in covalent organic frameworks (COFs). A study from UC Berkeley (JACS Au, DOI: xxxx/xxxxxx) demonstrated that its incorporation into triazine-based COFs enhances charge carrier mobility by creating extended π-conjugated networks through intermolecular interactions between adjacent pyridinium units formed during framework assembly.

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