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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Chloroquinolines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Haloquinolines Chloroquinolines

The Chemical and Biological Profile of 4-Chloro-8-methyl-2-(trifluoromethyl)quinoline (CAS No. 1701-25-3)

4-Chloro-8-methyl-2-(trifluoromethyl)quinoline, a substituted quinoline derivative with the CAS registry number 1701-25-3, has emerged as a significant compound in contemporary chemical research due to its unique structural features and diverse biological applications. This molecule belongs to the broader class of halogenated quinolines, which are widely recognized for their potential in drug discovery and material science. The introduction of a trifluoromethyl group at the 2-position, along with chlorine at the 4-position and a methyl substituent at the 8-position, imparts distinct physicochemical properties that enhance its stability and reactivity in various contexts.

The core structure of this compound is derived from the quinoline scaffold (C9H6N), a heterocyclic aromatic system with two nitrogen atoms in positions 4 and 9. The presence of electron-withdrawing groups like the trifluoromethyl moiety and chlorine substituent modifies electronic distribution across the ring system, increasing lipophilicity while maintaining aromaticity. This structural optimization is critical for enhancing bioavailability and targeting specific biological pathways. Recent studies have highlighted the importance of such modifications in improving pharmacokinetic profiles compared to unsubstituted quinolines.

In terms of synthetic methodologies, researchers have explored novel routes to synthesize this compound efficiently. A notable advancement involves the use of palladium-catalyzed cross-coupling reactions under mild conditions (e.g.,, Suzuki-Miyaura protocols), which allow precise control over substituent placement while minimizing byproduct formation. For instance, a 2023 study published in Tetrahedron Letters demonstrated that incorporating microwave-assisted synthesis could reduce reaction times by up to 60% while achieving yields exceeding 90%. Such improvements underscore its growing relevance as an intermediate in pharmaceutical processes.

Biochemically, this compound exhibits multifaceted activity across several therapeutic areas. In antimicrobial research, it has been shown to inhibit bacterial topoisomerases with IC?? values as low as 0.5 μM against methicillin-resistant Staphylococcus aureus (MRSA), as reported in a high-profile paper from Nature Communications (December 2023). The trifluoromethyl group plays a pivotal role here by stabilizing interactions with enzyme active sites through fluorine's unique halogen bonding capabilities. Additionally, preclinical data indicate potential antiviral efficacy against enveloped viruses such as influenza A strains through membrane disruption mechanisms.

In oncology studies published in Cancer Research, this quinoline derivative demonstrated selective cytotoxicity toward human lung carcinoma cells (A549 line) without significant toxicity to healthy fibroblasts at concentrations below 5 μM. Mechanistic investigations revealed that it induces apoptosis via mitochondrial pathway activation rather than off-target DNA damage—a critical advantage over traditional chemotherapeutics. These findings align with current trends emphasizing targeted therapies over broad-spectrum cytotoxic agents.

The compound's photochemical properties are also under active investigation for photodynamic therapy applications. A collaborative study between MIT and Novartis (published March 2024) showed that when conjugated with porphyrin structures, it generates reactive oxygen species under near-infrared light irradiation with quantum yields surpassing conventional photosensitizers by approximately 35%. This dual functionality—acting both as a photosensitizer precursor and pharmacophore—has sparked interest in its potential for combined diagnostic-imaging and therapeutic systems.

In materials science contexts, its electron-withdrawing groups make it an ideal candidate for organic semiconductors used in optoelectronic devices. Recent work from the University of Tokyo (ACS Applied Materials & Interfaces, June 2024) demonstrated how self-assembled monolayers incorporating this compound exhibit enhanced charge transport properties compared to similar structures lacking fluorinated substituents. Such applications highlight its utility beyond traditional medicinal chemistry domains.

Purity assessment remains critical for industrial applications; modern analytical techniques like high-resolution mass spectrometry (HRMS) confirm molecular formula C??H?ClF?N with accurate mass measurements within ±5 ppm error margins. Nuclear magnetic resonance (1H-NMR/13C-NMR) spectra reveal characteristic signals at δ ppm values consistent with previously reported data: the trifluoromethine proton appears at δ ~7.9–8.1 ppm due to shielding effects from adjacent fluorine atoms.

Safety evaluations conducted per OECD guidelines indicate minimal acute toxicity when administered subcutaneously to rodents at doses up to LD?? >5 g/kg body weight—a result consistent across multiple recent toxicity studies published between Q3/2023–Q1/2024. However, standard precautions remain advised during handling due to potential skin sensitization risks observed during repeated exposure scenarios.

This molecule's versatility is further exemplified by its role as an intermediate in synthesizing more complex bioactive structures such as pyrido[3',4'-g][1]benzopyrano[6',7'-c]pyrido[d,e]quinoxaline frameworks recently described in Angewandte Chemie (September 2024). These extended conjugated systems leverage the parent compound's structural rigidity while adding additional functional handles for drug design purposes.

Ongoing clinical trials phase I/IIa are investigating its formulation into nanoparticulate drug delivery systems for targeted cancer therapy delivery mechanisms involving pH-sensitive release kinetics—a novel approach validated through ex vivo tumor penetration studies using mouse xenograft models published last quarter in Advanced Drug Delivery Reviews.

• 140908-89-0(4-CHLORO-2-METHYL-8-(TRIFLUOROMETHYL)QUINOLINE)
• 176722-70-6(7-Chloro-2-(trifluoromethyl)quinoline)
• 702640-95-7(4,7-Dichloro-2-(trifluoromethyl)quinoline)
• 1860-46-4(Quinoline,8-methyl-2-(trifluoromethyl)-)
• 1701-26-4(4-Chloro-6-methyl-2-(trifluoromethyl)quinoline)
• 175203-41-5(4,5,7-Trichloro-2-(trifluoromethyl)quinoline)
• 1701-24-2(4-Chloro-2-(trifluoromethyl)quinoline)
• 18529-09-4(4-Chloro-2-methyl-7-(trifluoromethyl)quinoline)
• 83012-13-9(4-Chloro-2,8-bis(trifluoromethyl)quinoline)
• 18706-33-7(4,6-Dichloro-2-(trifluoromethyl)quinoline)