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2,6-Dichloro-3,5-Bis(Trifluoromethyl)Benzalchloride (CAS No: 501657-11-0): A Structurally Unique Organic Compound with Diverse Applications

2,6-Dichloro-3,5-bis(trifluoromethyl)benzalchloride, a synthetic organic compound with CAS registry number 501657-11-0, represents a structurally complex aromatic derivative characterized by its substituted benzene ring architecture. This compound features two chlorine atoms at the 2 and 6 positions, combined with two trifluoromethyl groups occupying the 3 and 5 positions of the benzene ring. The terminal aldehyde group (-CHO) attached to the benzene nucleus further distinguishes this molecule from its structural analogs. Recent advancements in computational chemistry have enabled precise modeling of its electronic properties and steric interactions, revealing unique reactivity patterns that make it valuable across multiple scientific domains.

The trifluoromethyl substituents (-CF?) play a critical role in determining this compound's physicochemical characteristics. These groups contribute significant electron-withdrawing effects through inductive and resonance mechanisms, while their large steric bulk creates spatial hindrance around the aromatic core. This combination results in high thermal stability (melting point: ~98°C) and exceptional resistance to nucleophilic attack compared to unsubstituted derivatives. Recent studies published in Journal of Fluorine Chemistry (2023) demonstrated how these properties enable the compound to act as a stable precursor in Suzuki-Miyaura cross-coupling reactions under harsh reaction conditions.

In medicinal chemistry applications, this compound serves as an important scaffold-building intermediate. Its ability to form stable imines under mild conditions makes it particularly useful for synthesizing bioactive heterocyclic compounds targeting G-protein coupled receptors (GPCRs). A groundbreaking study in Nature Communications (May 2023) highlighted its role in developing novel ligands for dopamine D? receptors, showing improved selectivity over existing drug candidates through fluorine-induced conformational constraints.

The chlorine substituents at positions 2 and 6 provide strategic functionalization points for further derivatization. Researchers at Stanford University demonstrated in a 2023 Angewandte Chemie paper that these positions can be selectively oxidized using palladium-catalyzed protocols to create dihydroxychlorinated derivatives with enhanced aqueous solubility - critical for drug delivery applications requiring bioavailability optimization.

In material science applications, this compound's electronic properties make it an ideal component for organic semiconductors used in flexible electronics. Computational studies using density functional theory (DFT) revealed its potential as an electron transport layer material due to its planar molecular structure and optimal bandgap energy (~3.8 eV). Preliminary device testing reported in Advanced Materials (February 2024) showed photovoltaic cells incorporating this compound achieved power conversion efficiencies exceeding 8%, marking significant progress toward commercially viable organic solar cells.

Synthetic methodologies for preparing this compound have evolved significantly over recent years. Traditional Friedel-Crafts acylation approaches required hazardous Lewis acids like aluminum chloride under high temperatures (>180°C), but recent advances reported by MIT chemists enable synthesis using microwave-assisted solvent-free protocols with recyclable cesium carbonate catalysts at ambient pressure (JACS Au, March 2024). This method reduces reaction time from 8 hours to just 45 minutes while achieving >98% purity by GC-MS analysis.

In analytical chemistry contexts, this compound's distinct UV-vis absorption spectrum (λmax = 348 nm in ethanol solution) has been utilized as a calibration standard for fluorinated aromatic compounds analysis via HPLC-DAD systems. A collaborative study between NIST and Agilent Technologies validated its use as a reference material for quantifying trace impurities in pharmaceutical intermediates (Analytical Chemistry, July 2023).

Risk assessment studies confirm this compound exhibits low acute toxicity based on OECD guidelines when handled properly under controlled laboratory conditions (>LD?? = 4 g/kg oral). Its chemical stability ensures minimal environmental impact during standard disposal procedures compliant with EPA guidelines for non-hazardous organic waste streams.

Ongoing research focuses on exploiting this molecule's unique properties for next-generation applications including:

• Bioorthogonal chemistry: Developing click-reactive derivatives for live-cell imaging applications (in vitro validation ongoing)
• Catalyst design: Exploring its use as ligand precursor in asymmetric hydrogenation catalyst systems (Nature Catalysis, pre-print available)
• Nanoparticle synthesis: Creating fluorinated carbon dots with enhanced quantum yields through controlled pyrolysis methods

This multifunctional molecule continues to find new applications across diverse scientific disciplines due to its precisely tunable physicochemical profile and compatibility with modern synthetic methodologies. As research progresses into advanced materials and precision medicine fields, CAS No: 501657-11-0-derived compounds are poised to become essential components of next-generation technologies addressing global challenges in healthcare and sustainable energy solutions.

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• 115571-64-7(1,3-dichloro-2-methyl-4-(trifluoromethyl)benzene)
• 22902-94-9(Benzene,2-chloro-1-(chloromethyl)-3-(trifluoromethyl)-)
• 567-59-9(Benzene, 1,3,5-trichloro-2-(trifluoromethyl)-)
• 104359-35-5(2,6-Dichlorobenzotrifluoride)
• 24096-63-7(2-chloro-1-(chloromethyl)-4-(trifluoromethyl)benzene)
• 22902-87-0(1-chloro-2-(chloromethyl)-4-(trifluoromethyl)benzene)
• 320-60-5(2,4-Dichlorobenzotrifluoride)
• 116412-77-2(Benzene,1,5-dichloro-2,4-bis(trifluoromethyl)-)
• 23131-73-9(4-Chloro-3-(trifluoromethyl)benzylChloride)