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  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
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  A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives

Comprehensive Analysis of 4-(Difluoromethoxy)-3-methoxybenzoyl Chloride (CAS No. 162401-79-8): Properties, Applications, and Industry Trends

The chemical compound 4-(difluoromethoxy)-3-methoxybenzoyl chloride (CAS No. 162401-79-8) is a specialized benzoyl chloride derivative with significant relevance in modern organic synthesis and pharmaceutical research. This fluorinated aromatic intermediate has garnered attention due to its unique molecular structure, combining a difluoromethoxy group and a methoxy substituent on the benzene ring, which imparts distinct electronic and steric properties. As researchers increasingly explore fluorine-containing compounds for their enhanced bioavailability and metabolic stability, this compound has emerged as a valuable building block in drug discovery pipelines.

From a structural perspective, 4-(difluoromethoxy)-3-methoxybenzoyl chloride features a reactive acyl chloride moiety (-COCl) at position 1 of the benzene ring, making it highly effective for amide bond formation and esterification reactions. The difluoromethoxy group (-OCF₂H) at position 4 and the methoxy group (-OCH₃) at position 3 create an electron-rich aromatic system that influences both its reactivity and applications. This configuration aligns with current trends in medicinal chemistry, where such modified benzoyl chlorides are employed to develop targeted therapeutics with improved pharmacokinetic profiles.

The synthesis of 162401-79-8 typically involves multi-step processes starting from vanillin or related methoxybenzaldehyde derivatives, incorporating fluorination techniques followed by controlled oxidation to the acyl chloride. Recent advancements in continuous flow chemistry have optimized its production, addressing common challenges like moisture sensitivity—a critical consideration given the compound's tendency to hydrolyze to the corresponding carboxylic acid. These process improvements resonate with industry demands for sustainable chemical manufacturing and green chemistry principles.

In pharmaceutical applications, this compound serves as a key intermediate for biologically active molecules, particularly in developing kinase inhibitors and G-protein-coupled receptor (GPCR) modulators. Its difluoromethoxy group enhances membrane permeability—a property highly sought after in CNS drug development—while the methoxy group contributes to target binding affinity. These characteristics explain its growing presence in patents for neurodegenerative disease treatments and metabolic disorder therapies, aligning with global health priorities.

The material science sector has also explored 4-(difluoromethoxy)-3-methoxybenzoyl chloride for creating advanced polymeric materials with tailored dielectric properties. The fluorine atoms impart thermal stability and chemical resistance to resulting polymers, making them suitable for high-performance coatings and electronic encapsulation materials. This dual applicability in life sciences and advanced materials reflects the compound's versatility—a frequent search topic among specialty chemical researchers.

Quality control for CAS No. 162401-79-8 requires rigorous analytical methods, with HPLC purity analysis and 19F NMR spectroscopy being particularly important due to the fluorine content. Storage recommendations emphasize anhydrous conditions at controlled temperatures, typically under inert atmosphere—details often queried by laboratory professionals. The compound's spectroscopic fingerprints (IR: ~1780 cm^-1 for C=O stretch; ¹H NMR: δ 3.9 for OCH₃) serve as important identification markers for users.

Emerging research directions include exploring this compound's potential in catalyzed cross-coupling reactions and as a precursor for fluorescent probes. The scientific community has shown particular interest in its use for creating PET radiotracers (positron emission tomography), where the difluoromethoxy group can be replaced with ¹⁸F-labeled analogs—a hot topic in molecular imaging research. Such applications demonstrate how fundamental benzoyl chloride chemistry continues to enable cutting-edge technologies.

From a commercial perspective, 4-(difluoromethoxy)-3-methoxybenzoyl chloride remains a low-volume high-value chemical, with pricing reflecting the specialized nature of its production and handling requirements. Suppliers typically offer custom synthesis services and GMP-grade quantities to meet diverse research needs, with purity specifications often exceeding 97%. These market dynamics interest professionals searching for pharmaceutical intermediates or custom synthesis solutions.

Environmental and handling considerations for this compound focus on standard laboratory safety protocols for reactive acyl chlorides, without the restrictions associated with controlled substances. Proper waste disposal methods and engineering controls (e.g., glove boxes for moisture-sensitive work) represent frequent search queries related to its practical use. These operational aspects complement the scientific interest in its applications.

Looking forward, the compound's trajectory appears closely tied to developments in fluorine chemistry and precision medicine. As drug discovery increasingly emphasizes structure-property relationships, the unique features of 162401-79-8—particularly its balanced lipophilicity from the difluoromethoxy group—will likely sustain its importance. The growing database of structure-activity relationship (SAR) studies incorporating this scaffold further validates its utility as researchers address complex therapeutic targets.

• 3535-37-3(3,4-Dimethoxybenzoyl chloride)
• 57320-63-5(4-(Difluoromethoxy)benzoyl Chloride)
• 36823-88-8(4-(Trifluoromethoxy)benzoyl chloride)
• 50597-60-9(Benzoyl chloride, 4-hydroxy-3,5-dimethoxy-)
• 4521-61-3(3,4,5-Trimethoxybenzoyl chloride)
• 127163-51-3(2,2-Difluoro-1,3-benzodioxole-5-carbonyl chloride)
• 86270-03-3(3-(Trifluoromethoxy)benzoyl chloride)
• 1070774-23-0(4-methoxy-3-(trifluoromethoxy)benzoyl Chloride)
• 261951-93-3(2-Methyl-4-(trifluoromethoxy)benzoyl chloride)
• 289896-68-0(3-Hydroxy-4-methoxybenzoyl chloride)