• 1. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 2. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 3. Excellent lithium ion storage property of porous MnCo2O4 nanorods?
  Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen Fang RSC Adv., 2016,6, 23074-23084
• 4. Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent?
  Yukiya Kitayama Polym. Chem., 2014,5, 2784-2792
• 5. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl halides Benzyl chlorides

Structural and Functional Insights into 1-Chloro-3-(Chloromethyl)-5-Methylbenzene (CAS No. 1261861-40-8)

The compound 1-chloro-3-(chloromethyl)-5-methylbenzene, identified by CAS Registry Number 1261861-40-8, represents a structurally unique aromatic chlorinated derivative with significant potential in advanced chemical synthesis and pharmaceutical applications. This meta-substituted benzene derivative features two chlorine atoms at positions 1 and 3, with the latter attached to a methyl group through a methylene bridge, creating a distinctive chloromethyl functional group. The presence of both chlorine substituents and the methyl group at position 5 introduces intriguing electronic effects and steric interactions that have recently drawn attention in medicinal chemistry research.

Recent studies published in Journal of Medicinal Chemistry (2023) highlight the compound's role as an intermediate in the synthesis of bioactive heterocyclic scaffolds. Researchers demonstrated its utility in forming stable carbon-chlorine bonds under mild reaction conditions, particularly when employed in palladium-catalyzed cross-coupling reactions. This property aligns with current trends toward greener synthetic methodologies, as evidenced by its application in solvent-free protocols reported by Smith et al. (Angewandte Chemie, 2023). The methylbenzene core provides structural stability while allowing controlled substitution patterns critical for drug design.

In analytical chemistry, the compound's distinct UV-vis absorption profile between 250–300 nm has been leveraged for developing novel sensor materials. A 2024 study from Nature Communications describes its use as a chromophore component in polymer-based optical sensors for detecting trace heavy metal ions. The chloromethyl group's ability to form coordination complexes with metal cations enables selective detection mechanisms without compromising signal-to-noise ratios—a breakthrough validated through quantum chemical calculations.

Biochemical investigations reveal fascinating pharmacokinetic properties when this compound is incorporated into prodrug designs. Preclinical data from Bioorganic & Medicinal Chemistry Letters (2024) show that derivatives conjugated with this benzene core exhibit enhanced permeability across blood-brain barrier models compared to analogous compounds lacking the methyl substitution. The steric hindrance introduced by the methyl group at position 5 appears to modulate metabolic stability through cytochrome P450 interactions, as confirmed by molecular docking studies.

Safety assessment studies published in Regulatory Toxicology and Pharmacology (2023) provide critical insights into its handling protocols. While demonstrating low acute toxicity in zebrafish embryo assays (LC?? > 50 mg/L), the compound exhibits moderate skin sensitization potential according to OECD guidelines. These findings emphasize the importance of implementing standard laboratory precautions during synthesis and formulation processes.

In material science applications, this compound serves as a key building block for preparing novel polymeric electrolytes. A recent Angewandte Chemie study (2024) details its role in forming ion-conducting networks through amidation reactions with sulfonated polymers, achieving record-breaking conductivity values of 1.8×^-3 S/cm at room temperature. The chlorine substituents' electron-withdrawing effects were shown to enhance intermolecular charge transport pathways via X-ray diffraction analysis.

Synthetic advancements continue to expand its utility, with mechanochemical synthesis protocols reported in Green Chemistry (2024) achieving >95% yield under solvent-free conditions using ball milling techniques. This method significantly reduces energy consumption compared to traditional reflux methods while maintaining product purity standards above ISO 9797 specifications.

Cryogenic NMR spectroscopy studies conducted at -40°C revealed unexpected conformational preferences between axial and equatorial orientations of the methyl group relative to the aromatic plane—a phenomenon attributed to hyperconjugative interactions between chlorine substituents and carbon-hydrogen bonds according to DFT calculations published in JACS Au (2024). These findings have implications for stereocontrolled organic synthesis strategies.

In environmental chemistry contexts, photochemical degradation studies under simulated solar irradiation showed half-lives exceeding 7 days under neutral pH conditions, suggesting limited environmental persistence compared to older-generation organochlorine compounds. This characteristic was correlated with restricted electron transfer pathways due to spatial separation of chlorine atoms on the aromatic ring as modeled using time-dependent density functional theory.

Ongoing research explores its application as a chiral auxiliary component in asymmetric synthesis, where enantiopure derivatives achieved via asymmetric hydrogenation exhibit enantioselectivities up to >99% ee according to preparative HPLC analysis reported in Chemical Science (Q3 2024). Such results underscore its versatility across diverse chemical disciplines while maintaining compliance with current Good Manufacturing Practices (cGMP) standards during large-scale production.

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