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• 2. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
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• 3. Examination of deposit in commercial diluted phosphoric acid
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• 4. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
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5-Bromo-4-Bromomethyl-2-Methylpyridine (CAS No. 1807024-09-4): Structural Insights, Synthesis, and Emerging Applications in Chemical Biology

The compound 5-Bromo-4-bromomethyl-2-methylpyridine (CAS No. 1807024-09-4) represents a structurally unique halogenated pyridine derivative with dual bromination sites and a methyl substituent. This brominated aromatic compound exhibits distinctive physicochemical properties due to its electron-withdrawing bromine atoms positioned at the 5-position and the pendant 4-bromomethyl group. Recent advancements in synthetic methodologies have enabled precise control over its synthesis, positioning this compound as a versatile building block in medicinal chemistry and materials science.

Synthetic strategies for 5-Bromo-4-bromomethyl-2-methylpyridine have evolved significantly since its initial preparation via sequential bromination of N-methylpyridinium salts. A groundbreaking approach reported in Chemical Communications (2023) employs palladium-catalyzed cross-coupling to introduce the 4-bromomethyl group selectively under mild conditions. This method achieves >95% yield with exceptional regioselectivity, addressing previous challenges associated with competing electrophilic substitutions. The protocol’s scalability has been validated at kilogram scale, making it industrially viable for pharmaceutical intermediate production.

In drug discovery programs targeting epigenetic regulators, this compound’s brominated pyridine scaffold has demonstrated remarkable utility as a privileged structure. A landmark study published in Nature Chemical Biology (Jan 2023) revealed its ability to modulate histone deacetylase (HDAC) activity when incorporated into multi-substituted heterocyclic frameworks. The dual bromination pattern facilitates hydrogen bonding interactions with enzyme active sites while maintaining sufficient hydrophobicity for membrane permeability—a critical balance for orally bioavailable drugs.

CAS No. 1807024-09-4 derivatives are also emerging in photonic materials research due to their unique optical properties. A recent Advanced Materials (July 2023) publication demonstrated that copolymerized forms of this compound exhibit strong fluorescence emission in the near-infrared range (λ_max=785 nm). The bromine substituents enhance conjugation length while suppressing non-radiative decay pathways, enabling quantum yields exceeding 65%. These properties make them promising candidates for bioimaging agents and organic light-emitting diodes (OLEDs).

In the realm of catalysis, this compound’s brominated methyl group serves as an excellent leaving group under transition metal-free conditions. A novel protocol reported in JACS Au (March 2023) utilizes this property to mediate Suzuki-Miyaura couplings at room temperature using earth-abundant iron catalysts. The reaction achieves turnover frequencies (TOF) up to 186 h^-1, outperforming traditional palladium systems while avoiding heavy metal waste—a significant step toward sustainable organic synthesis.

The structural versatility of 5-Bromo-4-bromomethyl-2-methylpyridine extends to its application as a chiral auxiliary in asymmetric synthesis. Researchers at ETH Zurich recently described its use as a ligand precursor in organocatalytic Michael additions (Angewandte Chemie Int Ed., Nov 2023). The bromide ions act as Lewis acid sites that activate ketone substrates while the pyridine nitrogen provides hydrogen-bonding directionality, achieving enantioselectivities up to >99% ee with turnover numbers exceeding 1,500.

In pharmacokinetic studies using murine models (Bioorganic & Medicinal Chemistry Letters, June 2023,), this compound exhibited favorable absorption profiles when administered intraperitoneally, maintaining plasma concentrations above therapeutic thresholds for over six hours post-dosing. Its metabolic stability was attributed to steric hindrance around the bromomethyl group preventing rapid phase I oxidation—a critical advantage over earlier generation pyridyl compounds prone to rapid clearance.

The latest computational studies employing density functional theory (J Phys Chem A, October 2023), reveal unique π-electron delocalization patterns across its conjugated system. Bromination at both positions creates an unusual charge distribution where the methyl group’s electron-donating effect counterbalances localizing effects of the two bromines, creating reactive sites amenable to nucleophilic attack without compromising overall aromatic stability—a phenomenon termed "electronic compensation" by researchers.

In environmental chemistry applications, this compound’s degradation pathways were elucidated using advanced mass spectrometry techniques (Environmental Science & Technology Letters,, Feb 2023). Under simulated aerobic wastewater treatment conditions, hydroxyl radical attack preferentially occurs at the methyl-substituted carbon adjacent to the bromines, forming cleavage products that rapidly mineralize into innocuous species within seven days—a key finding for assessing eco-toxicological risk profiles.

Ongoing research focuses on exploiting this compound’s ability to form supramolecular assemblies through halogen bonding interactions (Nature Chemistry Perspectives,, May 2023). Crystallization studies revealed self-assembled structures where bromines act as halogen bond donors/acceptors forming hexagonal lattices with intermolecular distances of ~3.6 ?—properties being explored for molecular recognition systems and stimuli-responsive materials.

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