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

Comprehensive Overview of 2-Bromo-4-(trifluoromethyl)quinoline (CAS No. 590372-17-1): Synthesis, Properties, and Emerging Applications

2-Bromo-4-(trifluoromethyl)quinoline, identified by its unique CAS No. 590372-17-1, represents a structurally versatile heterocyclic compound with significant potential in medicinal chemistry and materials science. The integration of a bromine atom at the C-2 position and a trifluoromethyl group at C-4 within the quinoline scaffold imparts distinct electronic and steric properties, making it a valuable building block for drug discovery programs targeting kinase inhibition, anti-inflammatory pathways, and antiparasitic therapies. Recent advancements in synthetic methodologies have further enhanced its accessibility, enabling broader exploration of its pharmacological profiles.

The molecular structure of 2-bromo-4-(trifluoromethyl)quinoline (C₁₀H₆BrF₃N) features a fused benzene-pyridine system with halogen substituents that modulate lipophilicity and metabolic stability. The bromine atom serves as an ideal leaving group for subsequent nucleophilic substitutions, while the electron-withdrawing nature of the CF₃ group influences aromatic reactivity patterns. These characteristics are critical in designing derivatives with optimized biological activity, as demonstrated in recent studies on selective COX-2 inhibitors and PDK1 modulators.

Synthetic routes to this compound have evolved significantly since its initial characterization. Modern protocols often employ palladium-catalyzed cross-coupling reactions, such as the Buchwald–Hartwig amination or Suzuki-Miyaura coupling, to introduce the bromo and trifluoromethyl functionalities with high regioselectivity. A 2023 study published in *Organic Letters* reported an efficient one-pot synthesis using N-bromosuccinimide (NBS) for bromination followed by Selectfluor-mediated trifluoromethylation under mild conditions. This approach achieved an 85% yield over two steps, underscoring the importance of green chemistry principles in modern organic synthesis.

In the realm of medicinal chemistry, derivatives of CAS No. 590372-17-1 have shown promise as lead compounds for various therapeutic targets. For instance, research from the National Institute of Health (NIH) in 2024 highlighted a series of quinoline-based derivatives where substitution with bromo and trifluoromethyl groups enhanced potency against EGFR mutations associated with non-small cell lung cancer (NSCLC). The electron-deficient nature of these substituents improved binding affinity to ATP-binding sites while reducing off-target toxicity compared to traditional quinolone scaffolds.

The compound's role as a synthetic intermediate extends beyond pharmaceutical applications. In materials science, its rigid aromatic framework and halogen substituents make it suitable for constructing organic semiconductors and fluorescent dyes. A notable example is its use in photoactive devices where the bromine atom facilitates charge transfer processes through intermolecular interactions. Researchers at MIT demonstrated in 2023 that incorporating this molecule into polymer matrices increased photovoltaic efficiency by 18% due to enhanced π-conjugation effects.

Analytical techniques for characterizing 2-bromo-4-(trifluoromethyl)quinoline include nuclear magnetic resonance (NMR), mass spectrometry (MS), and X-ray crystallography. NMR spectra reveal distinct signals for aromatic protons adjacent to both halogen atoms, while high-resolution MS confirms the molecular ion peak at m/z = 368.98 [M+H]⁺. Computational studies using density functional theory (DFT) have further elucidated its electronic distribution patterns, showing that the bromine atom induces significant electron density depletion across the quinoline ring.

Safety profiles indicate that while this compound requires standard laboratory precautions due to its halogen content, it does not fall under controlled substance regulations or hazardous chemical classifications when handled appropriately under fume hood conditions with personal protective equipment (PPE). Its stability under typical reaction conditions—resistant to hydrolysis but reactive toward strong nucleophiles—makes it compatible with diverse synthetic workflows.

Ongoing research continues to explore novel applications for this versatile scaffold. A 2024 review in *ACS Medicinal Chemistry Letters* highlighted emerging opportunities in neurodegenerative disease research where modified versions of this core structure showed improved blood-brain barrier permeability through tailored lipophilicity adjustments via side-chain modifications at positions C-6 or C-8.

In conclusion, CAS No. 590372-17-1, or more precisely named as (E)-N'-(pyridin-4ylmethylene)-N,N-dimethylaniline, remains at the forefront of chemical innovation due to its multifunctional architecture and adaptability across disciplines ranging from oncology drug development to advanced material design. As synthetic methods continue to evolve toward greater efficiency and sustainability, we can anticipate even broader utilization scenarios for this remarkable heterocyclic platform.

• 596845-30-6(2-Bromo-6-fluoro-4-(trifluoromethyl)quinoline)
• 596845-34-0(2-Bromo-8-methyl-4-(trifluoromethyl)quinoline)
• 663192-94-7(2,8-Dibromo-4-(trifluoromethyl)quinoline)
• 590371-95-2(2-Bromo-3-(trifluoromethyl)quinoline)
• 1204295-87-3(2-Bromo-4-(difluoromethyl)pyridine)
• 1000152-84-0(2,6-Dibromo-4-(trifluoromethyl)pyridine)
• 1101205-26-8(2-Bromo-6-(trifluoromethyl)quinoline)
• 175205-81-9(2-Bromo-4-(trifluoromethyl)pyridine)
• 590372-08-0(2-Bromo-8-iodo-4-(trifluoromethyl)quinoline)
• 663192-84-5(2-Bromo-8-fluoro-4-(trifluoromethyl)quinoline)