Cas no 791595-93-2 (6-(trifluoromethyl)quinolin-2-amine)

6-(Trifluoromethyl)quinolin-2-amine is a versatile heterocyclic compound featuring a quinoline core substituted with a trifluoromethyl group at the 6-position and an amino group at the 2-position. The trifluoromethyl group enhances the molecule's lipophilicity and metabolic stability, making it valuable in medicinal chemistry and agrochemical applications. Its electron-withdrawing properties influence the electronic characteristics of the quinoline scaffold, potentially improving binding affinity in target interactions. The amino group provides a reactive site for further functionalization, enabling the synthesis of derivatives with tailored properties. This compound is particularly useful in the development of pharmaceuticals, such as kinase inhibitors or antimicrobial agents, due to its structural rigidity and bioisosteric potential. Its high purity and well-defined structure ensure reproducibility in research and industrial applications.
6-(trifluoromethyl)quinolin-2-amine structure
791595-93-2 structure
Product Name:6-(trifluoromethyl)quinolin-2-amine
CAS No:791595-93-2
MF:C10H7F3N2
MW:212.171192407608
MDL:MFCD11108685
CID:1016200
PubChem ID:11218095
Update Time:2025-11-01

6-(trifluoromethyl)quinolin-2-amine Chemical and Physical Properties

Names and Identifiers

    • 6-(trifluoromethyl)quinolin-2-amine
    • A849924
    • 6-(trifluoromethyl)quinolin-2-amine, 99%
    • AS-30848
    • EN300-7407708
    • BDBM50379207
    • SB70448
    • F2147-8836
    • Z1255430891
    • AKOS023554091
    • CHEMBL2011274
    • MFCD11108685
    • DTXSID80459077
    • 791595-93-2
    • SCHEMBL5683005
    • AMY26309
    • CS-0455817
    • DB-124165
    • MDL: MFCD11108685
    • Inchi: 1S/C10H7F3N2/c11-10(12,13)7-2-3-8-6(5-7)1-4-9(14)15-8/h1-5H,(H2,14,15)
    • InChI Key: IMXIFGHLRHXQGE-UHFFFAOYSA-N
    • SMILES: FC(C1C=CC2C(=CC=C(N)N=2)C=1)(F)F

Computed Properties

  • Exact Mass: 212.05613272g/mol
  • Monoisotopic Mass: 212.05613272g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 229
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.8
  • Topological Polar Surface Area: 38.9?2

Experimental Properties

  • Density: 1.5±0.1 g/cm3
  • Boiling Point: 349.0±42.0 °C at 760 mmHg
  • Flash Point: 164.8±27.9 °C
  • Vapor Pressure: 0.0±0.8 mmHg at 25°C

6-(trifluoromethyl)quinolin-2-amine Security Information

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Additional information on 6-(trifluoromethyl)quinolin-2-amine

Comprehensive Overview of 6-(Trifluoromethyl)quinolin-2-amine (CAS No. 791595-93-2)

6-(Trifluoromethyl)quinolin-2-amine (CAS No. 791595-93-2) is a fluorinated quinoline derivative that has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural and electronic properties. The compound features a trifluoromethyl group at the 6-position of the quinoline ring, which enhances its lipophilicity and metabolic stability, making it a valuable scaffold in drug discovery. Researchers are increasingly exploring its potential as a kinase inhibitor or antimicrobial agent, aligning with current trends in targeting resistant pathogens and precision medicine.

The quinoline-2-amine core of this compound is a privileged structure in medicinal chemistry, often associated with bioactivity against various disease targets. Recent studies highlight its role in modulating protein-protein interactions (PPIs), a hot topic in oncology and neurodegenerative disease research. The trifluoromethyl substitution further optimizes binding affinity, as evidenced by its prevalence in FDA-approved drugs like tofacitinib analogs. This aligns with the growing demand for fluorinated bioactive compounds in the pharmaceutical industry.

From a synthetic chemistry perspective, 791595-93-2 serves as a versatile intermediate for cross-coupling reactions and heterocyclic functionalization. Its stability under palladium-catalyzed conditions makes it ideal for constructing high-value N-heterocycles, a frequent search query among synthetic chemists. The compound’s electron-deficient quinoline ring also facilitates nucleophilic aromatic substitutions, a technique widely discussed in green chemistry forums aiming to reduce reaction steps.

Analytical characterization of 6-(Trifluoromethyl)quinolin-2-amine typically involves LC-MS and NMR spectroscopy, with the 19F NMR signal at ~-60 ppm serving as a diagnostic marker. This aspect resonates with researchers searching for fluorine NMR reference data or structure elucidation protocols. The compound’s UV absorption maxima near 270 nm also make it suitable for photophysical studies, connecting to emerging interests in fluorescent probes for bioimaging.

In material science, derivatives of 791595-93-2 have shown promise in organic electronics due to their electron-transport properties. This intersects with trending searches on OLED materials and small-molecule semiconductors. The trifluoromethyl group’s ability to tune HOMO-LUMO gaps is particularly relevant for designing n-type organic semiconductors, a key focus area in flexible electronics research.

Regulatory and safety assessments indicate that 6-(Trifluoromethyl)quinolin-2-amine requires standard handling precautions for laboratory chemicals. Its REACH compliance status and ecotoxicological profile are frequently queried by industrial users, reflecting broader concerns about sustainable chemical practices. The compound’s logP value (~2.8) suggests moderate bioavailability, a critical parameter in ADMET prediction workflows.

The commercial availability of CAS 791595-93-2 from specialty chemical suppliers has increased, driven by demand for building blocks in medicinal chemistry. Price trends and scale-up synthesis methods are common search terms associated with this compound, highlighting industry needs for cost-effective heterocyclic synthesis. Recent patent literature (2020-2023) describes its incorporation into JAK/STAT inhibitors and antifungal agents, validating its therapeutic relevance.

For researchers investigating structure-activity relationships (SAR), the 2-aminoquinoline moiety of 791595-93-2 offers multiple vectors for derivatization. This aligns with frequent queries about hydrogen bond donor/acceptor optimization in drug design. Computational studies suggest the compound’s potential as a metal-chelating pharmacophore, connecting to interests in metalloenzyme inhibitors.

Environmental fate studies of 6-(Trifluoromethyl)quinolin-2-amine are limited but suggest moderate persistence due to the C-F bond stability. This aspect relates to growing searches about fluorinated pollutant degradation, particularly among environmental chemists. The compound’s photostability under UV light makes it a candidate for photocatalysis studies, another trending research area.

In summary, 791595-93-2 represents a multifaceted compound bridging medicinal chemistry, materials science, and catalysis research. Its combination of quinoline bioactivity and trifluoromethyl effects addresses multiple contemporary scientific challenges, from drug resistance to energy-efficient electronics. Continued research will likely expand its applications in line with industry demands for multifunctional heterocycles.

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