• 1. 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
• 2. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 3. An integrated microfluidic 3D tumor system for parallel and high-throughput chemotherapy evaluation?
  Dan Liu,Rui Hu,Zhongchao Huang,Meilin Sun,Kai Han Analyst, 2020,145, 6447-6455
• 4. An aquatic host–guest complex between a supramolecular G-quadruplex and the anticancer drug doxorubicin?
  José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565
• 5. Alternative mixtures to R-600a. Theoretical assessment and experimental energy evaluation of binary mixtures in a commercial cooler: Mélanges alternatifs au R-600a. évaluation théorique et évaluation énergétique expérimentale de mélanges binaires dans un refroidisseur commercial.
  DanielCalleja-Anta,DanielSánchez,LauraNebot-Andres,RamónCabello,RodrigoLlopis

Introduction to 2-Methyl-4-(trifluoromethoxy)benzoyl chloride (CAS No. 261951-93-3) and Its Applications in Modern Chemical Biology

2-Methyl-4-(trifluoromethoxy)benzoyl chloride, identified by the Chemical Abstracts Service Number (CAS No.) 261951-93-3, is a specialized organic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its benzoyl chloride functional group and the presence of a methyl and trifluoromethoxy substituents, exhibits unique chemical properties that make it a valuable intermediate in the synthesis of various biologically active molecules.

The structure of 2-Methyl-4-(trifluoromethoxy)benzoyl chloride consists of a benzene ring substituted with a methyl group at the 2-position and a trifluoromethoxy group at the 4-position, further functionalized with a benzyloxychloride moiety. This specific arrangement imparts distinct reactivity, making it particularly useful in the formation of amide and ester bonds, which are fundamental in constructing complex pharmaceutical molecules.

In recent years, the demand for fluorinated compounds in drug development has surged due to their enhanced metabolic stability, lipophilicity, and binding affinity. The trifluoromethoxy group in 2-Methyl-4-(trifluoromethoxy)benzoyl chloride contributes to these desirable properties, making it an attractive building block for medicinal chemists. Moreover, the presence of the benzyloxychloride group facilitates its use in nucleophilic acyl substitution reactions, enabling the efficient synthesis of peptide mimetics and other bioactive peptides.

One of the most compelling applications of 2-Methyl-4-(trifluoromethoxy)benzoyl chloride is in the field of protease inhibition. Proteases are enzymes that play crucial roles in various biological pathways, and their inhibition is often a key strategy in developing anti-inflammatory, antiviral, and anticancer drugs. The compound’s ability to act as a substrate or inhibitor for certain proteases has been explored in several preclinical studies. For instance, researchers have investigated its potential as an inhibitor of matrix metalloproteinases (MMPs), which are involved in tissue degradation and are implicated in conditions such as arthritis and cancer metastasis.

Recent advancements in computational chemistry have also highlighted the utility of 2-Methyl-4-(trifluoromethoxy)benzoyl chloride in virtual screening campaigns. High-throughput virtual screening (HTVS) techniques allow for the rapid evaluation of large libraries of compounds against biological targets, identifying promising candidates for further experimental validation. The unique structural features of this compound make it a valuable candidate for such screens, particularly when targeting enzymes with specific binding pockets that can accommodate fluorinated aryl groups.

The synthesis of 2-Methyl-4-(trifluoromethoxy)benzoyl chloride typically involves multi-step organic transformations starting from commercially available precursors. A common synthetic route includes the chlorination of 2-methyl-4-hydroxybenzoic acid derivatives using reagents such as phosphorus oxychloride (POCl?). The introduction of the trifluoromethoxy group can be achieved through nucleophilic aromatic substitution reactions employing trifluoromethanol under acidic conditions. These synthetic strategies highlight the compound’s accessibility while maintaining high purity standards essential for pharmaceutical applications.

In addition to its role as a synthetic intermediate, 2-Methyl-4-(trifluoromethoxy)benzoyl chloride has been utilized in material science research. Fluorinated aromatic compounds are known for their thermal stability and electronic properties, making them suitable for applications in organic electronics and liquid crystal displays (LCDs). The benzyloxychloride functionality allows for further derivatization into polymers and coatings with enhanced durability and chemical resistance.

The growing interest in green chemistry has also prompted investigations into more sustainable synthetic methods for 2-Methyl-4-(trifluoromethoxy)benzoyl chloride. Researchers are exploring catalytic processes that minimize waste and reduce energy consumption. For example, transition metal-catalyzed cross-coupling reactions have been investigated as alternative pathways to construct the desired benzene ring derivatives efficiently.

Evaluation studies have demonstrated that 2-Methyl-4-(trifluoromethoxy)benzoyl chloride exhibits good solubility in common organic solvents such as dichloromethane and tetrahydrofuran (THF), which facilitates its use in various reaction conditions. Its stability under standard storage conditions further enhances its practicality as an industrial chemical intermediate. However, care must be taken to avoid moisture exposure, as benzoyl chlorides can hydrolyze to form benzoic acids and hydrochloric acid.

The impact of fluorine atoms on electronic properties has been extensively studied, particularly concerning their influence on regioselectivity and reactivity. In 2-Methyl-4-(trifluoromethoxy)benzoyl chloride, the electron-withdrawing nature of the trifluoromethoxy group modulates the electrophilicity of the carbonyl carbon, influencing its reactivity in nucleophilic additions. This feature has been exploited to develop asymmetric synthesis strategies where chiral auxiliaries or catalysts can direct selective transformations.

Future directions in research may focus on expanding the scope of applications for 2-Methyl-4-(trifluoromethoxy)benzoyl chloride by exploring its derivatives with different substituents or by incorporating it into novel drug candidates discovered through structure-based drug design approaches. Collaborative efforts between synthetic chemists and biologists will be crucial to unlocking its full potential across multiple disciplines.

• 57320-63-5(4-(Difluoromethoxy)benzoyl Chloride)
• 36823-88-8(4-(Trifluoromethoxy)benzoyl chloride)
• 76903-91-8(3-(difluoromethoxy)benzoyl chloride)
• 1261445-13-9(2-methyl-5-(trifluoromethoxy)benzoyl Chloride)
• 916420-52-5(3-methyl-5-(trifluoromethoxy)benzoyl Chloride)
• 86270-03-3(3-(Trifluoromethoxy)benzoyl chloride)
• 398156-36-0([1,1'-BIPHENYL]-4-CARBONYL CHLORIDE, 4'-(TRIFLUOROMETHOXY)-)
• 1261670-26-1(3'-(Trifluoromethoxy)-4-(trifluoromethyl)biphenyl-2-carbonyl chloride)
• 1070774-23-0(4-methoxy-3-(trifluoromethoxy)benzoyl Chloride)
• 886503-20-4(3-Chloro-5-(trifluoromethoxy)benzoyl chloride)