• 1. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143
• 2. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 3. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
• 4. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 5. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives Chlorinated biphenyls

Introduction to 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid (CAS No. 273727-25-6)

4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid, identified by its Chemical Abstracts Service (CAS) number 273727-25-6, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and medicinal chemistry. This compound belongs to the class of benzoic acid derivatives, characterized by its structural complexity and functional diversity. The presence of both chloro and trifluoromethyl substituents on the aromatic ring imparts unique electronic and steric properties, making it a valuable scaffold for the development of novel bioactive molecules.

The benzoic acid moiety is a well-documented pharmacophore in drug discovery, known for its role in modulating various biological pathways. Specifically, benzoic acid derivatives have been extensively studied for their potential in anti-inflammatory, analgesic, and antimicrobial applications. The introduction of a chloro group at the 4-position enhances the lipophilicity and metabolic stability of the molecule, while the 4-trifluoromethylphenyl group further contributes to its binding affinity by increasing the electron-withdrawing effect and reducing rotameric flexibility.

In recent years, 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid has been explored as a key intermediate in the synthesis of pharmacologically active compounds. Its structural features make it an ideal candidate for further functionalization, allowing chemists to tailor its properties for specific therapeutic targets. For instance, modifications at the carboxylic acid group can yield esters or amides, which are common pharmacological moieties found in approved drugs.

One of the most compelling aspects of this compound is its utility in the development of small-molecule inhibitors targeting enzyme-catalyzed pathways. The trifluoromethyl group, in particular, is known to improve binding interactions by enhancing hydrophobic interactions and reducing metabolic susceptibility. This has led to its incorporation into molecules designed to inhibit kinases and other enzymes implicated in cancer and inflammatory diseases. Recent studies have demonstrated promising results in using derivatives of 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid as lead compounds for kinase inhibitors, with several preclinical candidates showing encouraging activity profiles.

The synthesis of 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid typically involves multi-step organic transformations, starting from commercially available aromatic precursors. The chlorination step at the 4-position is often achieved using reagents such as phosphorus oxychloride (POCl?) or thionyl chloride (SOCl?), while the introduction of the trifluoromethylphenyl group can be accomplished via cross-coupling reactions like Suzuki or Buchwald-Hartwig couplings. These synthetic strategies highlight the compound's accessibility and versatility as a building block in medicinal chemistry.

From a computational chemistry perspective, 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid has been subjected to extensive molecular modeling studies to understand its interactions with biological targets. Quantum mechanical calculations have revealed that the electron-withdrawing nature of both chloro and trifluoromethyl groups significantly influences its binding affinity by modulating electronic distributions across the aromatic system. These insights have guided medicinal chemists in optimizing analogs for improved potency and selectivity.

The pharmacological potential of this compound has not gone unnoticed by academic and industrial researchers. Several groups have reported novel derivatives exhibiting anti-proliferative effects on cancer cell lines, with some showing comparable or even superior activity compared to existing therapeutic agents. The carboxylic acid functionality also allows for further derivatization into prodrugs or conjugates designed to enhance bioavailability or target specificity. Such modifications are critical for translating laboratory findings into viable clinical candidates.

In addition to its role in oncology research, 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid has been explored for its anti-inflammatory properties. Studies suggest that certain derivatives may inhibit cyclooxygenase (COX) enzymes or modulate cytokine production pathways, offering a potential therapeutic approach for chronic inflammatory conditions such as rheumatoid arthritis or inflammatory bowel disease. The combination of structural features from both benzoic acid and aromatic rings provides a rich chemical space for designing molecules with tailored biological activities.

The growing interest in 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid has also spurred innovation in synthetic methodologies aimed at improving yield and scalability. Continuous flow chemistry techniques have been particularly effective in producing this compound efficiently, reducing reaction times and minimizing waste generation. Such advancements align with broader trends in green chemistry, emphasizing sustainable practices in drug development.

Looking ahead, the future applications of 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid are likely to expand as new synthetic routes are developed and additional biological targets are explored. Its unique structural attributes make it a versatile scaffold for addressing unmet medical needs across multiple therapeutic areas. As research progresses, it is anticipated that more derivatives will enter clinical trials, bringing novel treatments to patients worldwide.

• 893637-96-2([1,1'-Biphenyl]-4-carboxylicacid, 4'-chloro-3'-(trifluoromethyl)-)
• 654-98-8(5-Chloro-2-(trifluoromethyl)benzoic acid)
• 1261439-83-1(5-Chloro-2'-(trifluoromethyl)-[1,1'-biphenyl]-3-carboxylic acid)
• 1261964-03-7(3-(4-Chlorophenyl)-5-trifluoromethylbenzoic acid)
• 1261930-84-0(3-(3,4-Dichlorophenyl)-5-trifluoromethylbenzoic acid)
• 1261477-13-7(4-chloro-3-[2-(trifluoromethyl)phenyl]benzoic Acid)
• 1261493-08-6(6-Chloro-2-(4-trifluoromethylphenyl)benzoic acid)
• 142994-09-0(4-Chloro-2-(trifluoromethyl)benzoic acid)
• 442670-42-0([1,1'-Biphenyl]-2-carboxylicacid, 3'-chloro-4'-(trifluoromethyl)-)
• 1261582-59-5(5-Chloro-3-(3-trifluoromethylphenyl)benzoic acid)