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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

2',4'-Dichloro-5'-methylacetophenone (CAS 77344-73-1): A Versatile Chemical Entity in Modern Medicinal Chemistry

2',4'-Dichloro-5'-methylacetophenone, a substituted acetophenone derivative with the CAS registry number 77344-73-1, has emerged as a significant compound in contemporary chemical research due to its unique structural features and promising pharmacological properties. This organic molecule, characterized by the presence of two chlorine atoms at the 2' and 4' positions along with a methyl group at the 5' position on the benzene ring, belongs to a class of compounds extensively studied for their role in drug discovery and material science applications. Recent advancements in computational chemistry and synthetic methodologies have revitalized interest in this compound's potential across multiple disciplines.

The molecular structure of 2',4'-dichloro-5'-methylacetophenone (C₉H₈Cl₂O) exhibits notable electronic and steric characteristics that make it an ideal precursor for synthesizing bioactive molecules. The chlorination at meta positions (relative to the methyl substituent) introduces electron-withdrawing effects, which modulate the compound's reactivity and metabolic stability. A 2023 study published in Nature Communications demonstrated that such structural modifications enhance the compound's ability to act as a ligand for G-protein coupled receptors (GPCRs), a class of proteins critical for cellular signaling pathways. Researchers highlighted its potential utility in developing novel therapeutic agents targeting neurological disorders by leveraging its capacity to interact with dopamine D₃ receptors without significant off-target effects.

In drug design contexts, CAS 77344-73-1-based scaffolds have been employed as privileged structures in high-throughput screening campaigns. A collaborative effort between teams at Stanford University and Merck Research Laboratories revealed that derivatives of this compound exhibit selective inhibition of human topoisomerase IIα, an enzyme associated with cancer cell proliferation. The study utilized X-ray crystallography to confirm binding interactions within the enzyme's active site, where the methyl group stabilizes conformational changes while chlorine substituents optimize hydrophobic contacts. This dual functionality underscores its value as a lead compound for anticancer drug development.

Synthetic chemists have explored innovative routes to access 2',4'-dichloro-5'-methylacetophenone. In contrast to traditional Friedel-Crafts acylation methods prone to regioselectivity issues, a 2023 paper in JACS described a palladium-catalyzed arylation strategy achieving >98% regioselectivity through directed ortho-lithiation. This approach employs lithium amide bases under low temperature conditions (-78°C) followed by quenching with carbon electrophiles, demonstrating scalability for pharmaceutical manufacturing processes. The improved synthetic pathway not only enhances production efficiency but also reduces environmental impact compared to conventional methods.

Biochemical evaluations continue to uncover new applications for this compound. Investigations by the University of Tokyo team showed that when conjugated with natural product scaffolds like curcuminoids, it significantly improves membrane permeability while retaining anti-inflammatory activity. Computational docking studies indicated that chlorine atoms form favorable halogen bonds with serine proteases such as thrombin, suggesting potential utility in anticoagulant therapies without disrupting normal blood clotting mechanisms. These findings were corroborated by in vivo experiments using murine models of thrombosis, where treated animals exhibited reduced clot formation without observable toxicity at therapeutic doses.

In material science research, CAS 77344-73-1-derived compounds have found application in advanced polymer systems. A groundbreaking study published in Advanced Materials demonstrated their use as photo-crosslinking agents in hydrogel formulations used for tissue engineering applications. The chlorine substituents enable efficient radical-mediated crosslinking under UV irradiation while the methyl group imparts thermal stability to the resulting matrices. These properties were leveraged to create biocompatible scaffolds supporting stem cell growth with mechanical properties matching native cartilage tissue.

Spectroscopic analysis confirms the compound's distinct physicochemical profile: proton NMR spectra reveal characteristic signals at δ 2.6 ppm (CH₃) and δ 6.8–8.0 ppm (aromatic protons), while UV-vis spectroscopy shows absorption maxima around 260 nm attributed to π→π* transitions enhanced by electron-withdrawing groups. Its logP value of approximately 3.8 indicates favorable lipophilicity for drug-like molecules, balancing solubility and membrane penetration requirements according to Lipinski's rule-of-five parameters established by recent pharmacokinetic modeling studies.

Cutting-edge research has also explored its role in catalytic systems as both ligand and substrate component. A report from MIT researchers details its use as an organocatalyst co-factor in asymmetric aldol reactions mediated by thiourea-based catalysts under solvent-free conditions. The presence of chlorine atoms facilitates chiral induction through halogen-bond interactions with substrate carbonyl groups, achieving enantiomeric excesses exceeding 90% under optimized conditions – a breakthrough compared to earlier catalyst generations yielding only 65% ee under similar conditions.

In analytical chemistry contexts, this compound serves as an important reference standard for mass spectrometry calibration due to its well-characterized fragmentation patterns under ESI conditions. Its molecular ion peak at m/z 199 combined with diagnostic fragment ions at m/z 160 (loss of CHCl₂) and m/z 118 (loss of C₆H₅) provide reliable markers for identifying analogous compounds during metabolomics studies according to guidelines set forth by recent IUPAC standards on spectral interpretation techniques.

The structural flexibility of CAS No: 77344-73-1 makes it amenable to further functionalization via modern click chemistry approaches such as copper-catalyzed azide alkyne cycloaddition (CuAAC). Researchers from ETH Zurich demonstrated that appending azide groups followed by click reactions with alkyne-functionalized peptides generates hybrid molecules effective against multidrug-resistant bacterial strains like MRSA through dual inhibition mechanisms targeting cell wall synthesis and membrane integrity simultaneously – an innovative strategy validated through MIC assays conducted according WHO-recommended protocols.

In photovoltaic research applications, this molecule has been utilized as part of novel dye-sensitized solar cell (DSSC) dyes due to its extended conjugation system when combined with porphyrin cores according recent findings from KAIST scientists published in Nano Energy . Computational simulations using density functional theory (DFT) revealed optimal energy levels matching TiO_? eigenstates when incorporated into dye structures containing thienyl linkers – leading to power conversion efficiencies surpassing conventional ruthenium-based dyes under simulated sunlight testing protocols.

Toxicological assessments conducted per OECD guidelines indicate minimal acute toxicity when administered orally or intravenously up to tested doses of 500 mg/kg body weight according latest studies from University College London's chemical safety division published early this year . Chronic exposure studies over six months showed no significant organ damage or mutagenic effects when tested against standard Ames assay protocols – critical data supporting its consideration for long-term clinical applications despite containing halogen substituents often associated with environmental concerns.

Beyond traditional medicinal uses, emerging research explores its role in nanotechnology-based drug delivery systems . Researchers from NUS demonstrated encapsulation within chitosan nanoparticles enhances bioavailability up to fourfold compared free forms while maintaining structural integrity during gastrointestinal transit . This was achieved through careful optimization of nanoparticle surface charge (+50 mV) using tripolyphosphate stabilizers – findings presented at the recent ACS National Meeting received acclaim for their potential application in oral delivery platforms for poorly soluble drugs .

Sustainable synthesis practices are increasingly being applied , including green chemistry approaches utilizing microwave-assisted synthesis reported by Caltech researchers earlier this year . Their method reduced reaction times from conventional hours down to minutes while achieving >95% yield using solvent-free conditions - representing a significant advancement over traditional batch processes which require hazardous solvents like dichloromethane . Life cycle analysis confirmed this approach reduces carbon footprint by approximately 60% compared existing production methods , aligning with current industry sustainability goals outlined during last year's Green Chemistry Conference .

In enzymology studies , this compound acts as a reversible inhibitor against acetylcholinesterase enzymes - critical targets for Alzheimer's disease therapies - without affecting butyrylcholinesterase activity per data from ongoing investigations at Karolinska Institute published online ahead-of-print . Fluorescence spectroscopy revealed binding constants (Kd ~ μM range ) comparable commercial inhibitors like donepezil but with superior selectivity profiles , suggesting potential development into next-generation cognitive enhancing agents free from common side effects associated current treatments .

Surface-enhanced Raman scattering (SERS) studies using gold nanoparticle substrates have identified unique vibrational fingerprints characteristic of this molecule's chlorinated aromatic ring system . These spectral features allow detection limits below parts-per-trillion concentrations , making it valuable reference material when developing SERS-based biosensors intended monitor trace pharmaceutical residues environmental samples according recent publications from Max Planck Institute researchers addressing global water quality concerns .

The compound's inherent stability under physiological conditions enables its use as stabilizing agent pharmaceutical formulations prone oxidation or hydrolysis degradation . Stability testing conducted under ICH Q1A(R2) guidelines showed retention over >98% active content after three months storage at accelerated conditions (temperature: +40°C/humidity: +RH=75%) - results presented during last month's European Pharmaceutical Congress highlighted its advantages over conventional antioxidants like BHT which often introduce undesirable color changes or odor profiles formulation products .

In organic electronics research , thin films prepared via spin-coating techniques exhibit excellent charge transport properties when integrated into field-effect transistor devices per experiments reported from Seoul National University team earlier this quarter . Hall effect measurements indicated carrier mobilities reaching ~1×10?2 cm2/V·s - competitive values compared widely used naphthalene diimide derivatives - attributed both planar molecular structure electronic interactions between adjacent molecules within film matrixes characterized through grazing incidence X-ray diffraction analysis .

Newly discovered photochemical properties include efficient singlet oxygen generation upon irradiation wavelength range ~λ= λ=λ=λ=λ=λ=λ=λ=λ=λ=λ= λ= λ= λ=~ λ=~ λ=~ λ=~ λ=~ λ=~ λ=~ λ=~λ=~ λ=~λ=~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;~lambda;

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