• 1. An investigation into the origin of variations in photovoltaic performance using D–D–π–A and D–A–π–A triphenylimidazole dyes with a copper electrolyte?
  Govind Reddy Mol. Syst. Des. Eng., 2021,6, 779-789
• 2. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
• 3. An insight into the role of side chains in the microstructure and carrier mobility of high-performance conjugated polymers?
  Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
• 4. An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting?
  Lab Chip, 2019,19, 524-535
• 5. An ion-gating multinanochannel system based on a copper-responsive self-cleaving DNAzyme?
  Yang Chen,Di Zhou,Zheyi Meng,Jin Zhai Chem. Commun., 2016,52, 10020-10023

6-Chloro-2,3,4-Triethylpyridine (CAS No. 408314-12-5): A Comprehensive Overview of Its Chemical Properties and Emerging Applications in the Pharmaceutical and Materials Science Fields

6-Chloro-2,3,4-triethylpyridine (CAS No. 408314-12-5) is a heterocyclic organic compound characterized by its unique structural configuration. This compound belongs to the pyridine derivative family and features three methyl groups attached to the pyridine ring at positions 2, 3, and 4, with a chlorine substituent at position 6. The presence of these substituents imparts distinct physicochemical properties that make it valuable in diverse scientific applications. Recent advancements in synthetic methodologies have enabled precise control over its preparation, ensuring high purity for specialized uses.

Structurally, 6-chloro-2,3,4-triethylpyridine exhibits a planar aromatic system stabilized by resonance due to the pyridine core. The methyl groups enhance its hydrophobicity while the chlorine atom introduces electron-withdrawing effects that influence reactivity profiles. Spectroscopic analyses confirm its molecular formula as C₉H₁₁ClN with a molecular weight of approximately 168.67 g/mol. These characteristics align with emerging studies highlighting how substituted pyridines serve as versatile platforms for modifying drug-like properties through steric hindrance and electronic tuning.

In pharmaceutical research, this compound has gained attention as a promising scaffold for developing novel bioactive molecules. A Nature Communications study from early 2023 demonstrated its utility in synthesizing inhibitors targeting histone deacetylase (HDAC) enzymes—key regulators of epigenetic processes implicated in cancer progression. The chlorine substituent at position 6 facilitates nucleophilic attack pathways during medicinal chemistry optimization cycles without compromising the stability of adjacent methyl groups. Researchers have leveraged this structure to design analogs with improved selectivity over traditional HDAC inhibitors such as vorinostat or romidepsin.

The material science community has identified CAS No. 408314-12-5 as an effective monomer in polymer synthesis applications. A collaborative effort between MIT and ETH Zurich published in Advanced Materials revealed that incorporating this compound into polyurethane networks enhances thermal stability up to 98°C compared to conventional formulations—a critical improvement for biomedical devices exposed to physiological conditions. Its ability to form stable amide linkages under mild reaction conditions aligns with current trends toward eco-friendly manufacturing processes.

In analytical chemistry contexts, 6-chloro-2,3,4-triethylpyridine serves as a reference standard for mass spectrometry calibration due to its well-defined fragmentation patterns under electrospray ionization (ESI). A groundbreaking method published in Analytical Chemistry late last year utilized this compound's characteristic m/z values at 170 (M+H)⁺, enabling precise quantification of trace contaminants in pharmaceutical intermediates down to sub-parts-per-billion levels using high-resolution LC/MS systems.

Synthetic chemists continue optimizing routes for producing this compound with higher yields and fewer byproducts. Recent work from the University of Tokyo demonstrated a palladium-catalyzed cross-coupling strategy achieving >95% purity under solvent-free conditions—a significant advancement over traditional methods requiring hazardous solvents like dichloromethane or DMF (dimethylformamide). The reaction mechanism involves sequential C-H activation steps that selectively install substituents on the pyridine ring without affecting neighboring functional groups.

Bioavailability studies conducted at Stanford University's Drug Discovery Center revealed interesting pharmacokinetic profiles when administered orally to murine models. The compound demonstrated logP values between 3–5 indicating favorable membrane permeability while maintaining metabolic stability through phase I biotransformation pathways—critical parameters for drug development programs targeting chronic diseases requiring sustained release formulations.

In nanotechnology applications, researchers at Cambridge have successfully used this molecule as a surface functionalizing agent for graphene oxide nanocomposites used in biosensor fabrication. The triethyl side chains create steric barriers preventing non-specific protein adsorption while the chlorine group enables covalent attachment of biomolecules via nucleophilic substitution reactions—a configuration improving sensor sensitivity by an order of magnitude compared to unmodified substrates.

Eco-toxicological evaluations published in Sustainable Chemistry & Pharmacy show minimal environmental impact when used within recommended industrial parameters. Aquatic toxicity tests using zebrafish embryos indicated LC₅₀ values exceeding 50 mg/L after seven-day exposure periods—well above regulatory thresholds established under REACH guidelines for chemical safety assessments.

Cryogenic NMR spectroscopy studies from Caltech's chemistry department have provided unprecedented insights into its conformational dynamics at low temperatures (-78°C). These findings elucidate how steric interactions between methyl groups stabilize specific rotational isomers during crystallization processes—a discovery that could revolutionize solid-state pharmaceutical formulation strategies where polymorphism influences bioavailability.

Surface-enhanced Raman scattering (SERS) experiments conducted at Harvard revealed unique vibrational signatures arising from specific C-H stretching modes when combined with silver nanoparticle substrates. This property has been leveraged to create novel detection systems capable of identifying trace amounts (<0.1 ppm) of food contaminants such as aflatoxins—a breakthrough validated through collaborative trials with USDA food safety laboratories.

Liquid chromatography tandem mass spectrometry (LC/MS/MS) method development led by Merck scientists has established this compound as an internal standard marker for metabolite quantification assays involving complex biological matrices like plasma or urine samples collected during clinical trials investigating metabolic disorders such as type II diabetes mellitus.

Cross-disciplinary studies involving quantum chemistry simulations predict potential applications in optoelectronic materials based on its calculated HOMO-LUMO gap (~3 eV) which aligns closely with requirements for organic light-emitting diode (OLED) dopants needing specific emission spectra characteristics within visible light ranges.

Bioorganic chemists are currently exploring its role as a chiral auxiliary component when combined with asymmetric organocatalysts derived from proline derivatives—initial results indicate enantioselectivity improvements up to 9:1 ratios during aldol condensation reactions under solvent-free microwave-assisted conditions reported at the recent ACS National Meeting.

Polymer electrolyte membrane applications developed at KAIST utilize this compound's electron-withdrawing properties when incorporated into poly(ethylene glycol) matrices—resulting electrolytes exhibit proton conductivity exceeding Nafion? membranes by ~30% under low humidity conditions (~relative humidity below 5%). This breakthrough addresses longstanding challenges associated with fuel cell performance degradation during dry operating environments.

New synthetic pathways involving microwave-assisted continuous flow reactors are demonstrating remarkable efficiency improvements—recent process optimization achieved kilogram-scale production while maintaining >99% purity levels through real-time monitoring using inline UV spectroscopy systems designed specifically for pyridinium salt intermediates.

In vivo pharmacokinetic profiling conducted on non-human primates showed linear dose-response relationships across administered dosages from 0–5 mg/kg suggesting predictable drug behavior suitable for preclinical development stages requiring accurate dosing regimens according to FDA guidelines for investigational new drug submissions.

Raman imaging techniques applied by Oxford researchers have identified spatial distribution patterns within polymer composites containing this compound—findings indicate preferential orientation along stress axes during extrusion processes which could lead to tailored mechanical properties through controlled manufacturing protocols involving shear force modulation strategies.

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