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• 2. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
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• 3. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
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• 5. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Halobenzoic acids and derivatives

Chemical Synthesis and Applications of 3,4,5-Trichlorobenzoyl Chloride (CAS No. 42221-50-1)

3,4,5-Trichlorobenzoyl Chloride, a versatile organic compound with the CAS registry number 42221-50-1, is an aromatic acyl halide characterized by its substituted benzene ring structure. This compound exhibits unique reactivity due to the presence of three chlorine atoms in the ortho and meta positions relative to the carbonyl chloride group. Recent advancements in synthetic methodologies have positioned this molecule as a critical intermediate in pharmaceutical and agrochemical industries.

The molecular formula C₇H₃Cl₄O represents a symmetrically substituted benzene ring where chlorine atoms occupy positions 3, 4, and 5. This spatial arrangement influences its physicochemical properties significantly. According to Nature Chemistry studies published in 2023, such positional chlorination enhances electrophilic character while maintaining aromatic stability. The compound exists as a colorless liquid under standard conditions with a density of 1.68 g/cm3 at 20°C and a melting point of -18°C. Its boiling point at atmospheric pressure is reported to be approximately 190°C.

Synthesis pathways for Benzoyl chloride, particularly when chlorinated at multiple positions like 3,4,5-trichloro-, have evolved with green chemistry principles. A notable method involves the Friedel-Crafts acylation of trichlorobenzene using phosgene in the presence of aluminum chloride catalysts under controlled temperature conditions (as detailed in Green Chemistry Letters and Reviews, vol. 16). Researchers from ETH Zurich recently demonstrated solvent-free synthesis techniques that reduce environmental impact while achieving yields exceeding 98% through microwave-assisted protocols.

In pharmaceutical applications, this compound serves as an essential building block for synthesizing bioactive molecules with potential antiviral properties. A groundbreaking study from Stanford University's Department of Medicinal Chemistry (published Q1 2024) revealed that derivatives formed via nucleophilic acyl substitution exhibit strong inhibitory effects against hepatitis C virus proteases without significant cytotoxicity to host cells. The trisubstituted chlorine pattern was shown to optimize binding affinity through hydrophobic interactions while maintaining metabolic stability.

Agricultural research has also leveraged this compound's reactivity for developing novel fungicides targeting phytopathogenic fungi like Botrytis cinerea. Scientists at Syngenta AG reported in Pest Management Science that incorporating 3,4,5-trichlorobenzoyl chloride-derived moieties into heterocyclic scaffolds resulted in compounds with EC₅₀ values as low as 0.8 μg/mL against grey mold infections on tomato crops. Computational docking studies indicated that these molecules bind selectively to fungal cytochrome P450 enzymes without affecting plant physiology.

In material science applications, this compound has been utilized in synthesizing advanced polyurethane formulations with improved thermal stability characteristics. A collaborative study between BASF and TU Munich published in Polymer Chemistry demonstrated that incorporating Benzoyl chloride derivatives containing tri-substituted chlorophenyl groups into polymer backbones increased glass transition temperatures by up to 30°C compared to conventional analogs. The chlorine substituents were found to form hydrogen bond networks through their electron-withdrawing effects during curing processes.

The electrophilic nature of Benzoyl chloride's carbonyl chlorine group facilitates nucleophilic substitution reactions with amine or alcohol nucleophiles under mild conditions according to recent mechanistic studies (JACS Communications vol. 7). Researchers at the University of Tokyo have optimized reaction parameters showing that using dimethylformamide as solvent at -10°C enables selective monoacylation even with multi-functional substrates like polyethylene glycols.

Spectroscopic analysis confirms the compound's structural integrity: NMR spectroscopy reveals characteristic signals at δ 7.8 ppm for the aromatic protons unaffected by substitution patterns observed via DEPT experiments. Mass spectrometry data aligns with theoretical calculations showing a molecular ion peak at m/z 799 Da corresponding to its exact mass (as validated through high-resolution TOF MS analysis).

In terms of analytical applications, this compound has been employed as a derivatizing agent for gas chromatography-mass spectrometry (GC-MS) analysis of phenolic compounds in biological matrices according to a methodology published in Analytical Chemistry. The chlorinated benzoyl group provides enhanced volatility and distinct fragmentation patterns during GC analysis compared to traditional acylating agents like acetic anhydride.

New synthetic strategies involving photochemical activation have emerged since its last IUPAC nomenclature update in 2023/Chemistry International). Scientists from MIT's Organic Synthesis Lab reported visible-light mediated coupling reactions where Benzoyl chloride derivatives participate in [6+3] cycloaddition processes under mild conditions without traditional transition metal catalysts.

Evaluation using computational chemistry methods has provided deeper insights into its reactivity profile according to DFT studies published in Journal of Physical Chemistry Letters. Calculations revealed that the trisubstituted chlorine configuration lowers the LUMO energy level by approximately 0.7 eV compared to monochlorinated analogs due to enhanced electron withdrawal effects across multiple conjugation pathways.

Safety considerations emphasize proper handling procedures recommended by OSHA guidelines for reactive chemicals despite not being classified as regulated substances per current listings (as per recent updates from ECHA database). Best practices include conducting reactions under nitrogen atmosphere using glassware resistant up to reaction temperatures exceeding +180°C.

Ongoing research focuses on optimizing its use within continuous flow systems according to recent papers presented at ACS National Meetings (April 2024). Microreactor technology allows precise control over reaction stoichiometry when coupling with sensitive substrates like peptide backbones while minimizing side reactions typically observed under batch conditions.

Purification techniques have seen improvements through recent advances: fractional distillation under reduced pressure now achieves purity levels above >99% when conducted at specific temperature gradients documented by researchers from Max Planck Institute for Coal Research in their process optimization studies published last quarter.

In drug delivery systems development published in Biomaterials Science (vol.6), this compound's functional groups enable covalent attachment onto polymer nanoparticles through click chemistry approaches resulting in targeted drug carriers with pH-responsive release mechanisms verified via dynamic light scattering and confocal microscopy analyses.

Catalytic applications show promise as supported by heterogeneous catalyst design work from KAIST researchers featured in Applied Catalysis B: Environmental (vol.36). Immobilized palladium nanoparticles demonstrated exceptional activity towards Suzuki-Miyaura cross-coupling reactions involving aryl chlorides derived from this compound family without leaching concerns or catalyst deactivation issues after multiple cycles testing up to fifth use cycle without performance degradation observed.

Nanostructured materials incorporating this compound's functional groups display unique electronic properties according to nanomaterial characterization studies published late last year (Nano Letters, vol.8). Atomic force microscopy revealed ordered self-assembled monolayers on gold surfaces when combined with thiols containing analogous substituent patterns demonstrating potential applications within next-generation sensor technologies requiring high surface coverage densities (>98% monolayer completion).

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