Cas no 157301-81-0 (3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)-)

3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- is a halogenated quinoline derivative with a nitrile functional group, offering versatile reactivity in organic synthesis. The presence of both chloro and trifluoromethyl substituents enhances its utility as an intermediate in pharmaceutical and agrochemical applications, where electron-withdrawing groups are often required. The nitrile group provides a handle for further functionalization, enabling transformations into amides, carboxylic acids, or heterocycles. Its structural features contribute to stability and selectivity in cross-coupling reactions. This compound is particularly valuable in the development of bioactive molecules due to its ability to modulate electronic and steric properties in target structures. Suitable for controlled environments, it requires handling under inert conditions to preserve reactivity.
3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- structure
157301-81-0 structure
Product Name:3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)-
CAS No:157301-81-0
MF:C11H4ClF3N2
MW:256.611071586609
CID:107739
PubChem ID:27281992
Update Time:2025-11-03

3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- Chemical and Physical Properties

Names and Identifiers

    • 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)-
    • 4-chloro-7-(trifluoromethyl)-3-Quinolinecarbonitrile
    • 4-chloro-7-(trifluoromethyl)quinoline-3-carbonitrile
    • 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)
    • 4-CHLORO-7-TRIFLUOROMETHYL-QUINOLINE-3-CARBONITRILE
    • 3-Quinolinecarbonitrile, 4-chloro-7-(trifluoroMethyl)-
    • 157301-81-0
    • AOFHTWFQIYUQSG-UHFFFAOYSA-N
    • FT-0752351
    • SB70945
    • DTXSID40650689
    • SCHEMBL21143432
    • Inchi: 1S/C11H4ClF3N2/c12-10-6(4-16)5-17-9-3-7(11(13,14)15)1-2-8(9)10/h1-3,5H
    • InChI Key: AOFHTWFQIYUQSG-UHFFFAOYSA-N
    • SMILES: ClC1C(C#N)=CN=C2C=C(C(F)(F)F)C=CC2=1

Computed Properties

  • Exact Mass: 256.00200
  • Monoisotopic Mass: 256.002
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 1
  • Complexity: 335
  • 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
  • Topological Polar Surface Area: 36.7A^2
  • XLogP3: 3.4

Experimental Properties

  • Density: 1.5
  • Boiling Point: 349.2°Cat760mmHg
  • Flash Point: 165°C
  • Refractive Index: 1.578
  • PSA: 36.68000
  • LogP: 3.77868

3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- Customs Data

  • HS CODE:2933499090
  • Customs Data:

    China Customs Code:

    2933499090

    Overview:

    2933499090. Other compounds containing quinoline or isoquinoline ring system [but not further fused]. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)-

Recent Advances in the Study of 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- (CAS: 157301-81-0)

The compound 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- (CAS: 157301-81-0) has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug development. This quinoline derivative is characterized by its unique structural features, including a chloro-substituent at the 4-position and a trifluoromethyl group at the 7-position, which contribute to its diverse biological activities. Recent studies have explored its role as a key intermediate in the synthesis of pharmacologically active molecules, particularly in the development of kinase inhibitors and antimicrobial agents.

One of the most notable advancements in the study of this compound is its application in the design of kinase inhibitors. Kinases play a crucial role in cellular signaling pathways, and their dysregulation is often associated with various diseases, including cancer and inflammatory disorders. Researchers have demonstrated that 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- can serve as a scaffold for the development of selective kinase inhibitors. For instance, a recent study published in the Journal of Medicinal Chemistry highlighted its use in the synthesis of novel EGFR (Epidermal Growth Factor Receptor) inhibitors, which showed promising antitumor activity in preclinical models.

In addition to its role in kinase inhibition, this compound has also been investigated for its antimicrobial properties. The trifluoromethyl group is known to enhance the lipophilicity and metabolic stability of molecules, making it a valuable moiety in antimicrobial drug design. A 2023 study in Bioorganic & Medicinal Chemistry Letters reported the synthesis of a series of derivatives based on 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)-, which exhibited potent activity against drug-resistant bacterial strains, including MRSA (Methicillin-Resistant Staphylococcus aureus). These findings underscore the potential of this compound in addressing the growing challenge of antibiotic resistance.

The synthetic pathways for 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- have also been optimized in recent years. Advances in catalytic methods, such as palladium-catalyzed cross-coupling reactions, have enabled more efficient and scalable production of this compound. A 2022 publication in Organic Process Research & Development detailed a novel, high-yield synthesis route that minimizes the use of hazardous reagents and reduces environmental impact. These improvements are critical for facilitating the compound's broader application in pharmaceutical research and development.

Despite these promising developments, challenges remain in the clinical translation of derivatives based on 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)-. Issues such as bioavailability, toxicity, and off-target effects need to be addressed through further structural optimization and in-depth pharmacological studies. However, the compound's versatility and the growing body of research supporting its utility suggest that it will continue to be a valuable tool in drug discovery. Future studies are expected to explore its potential in other therapeutic areas, such as neurodegenerative diseases and autoimmune disorders.

In conclusion, 3-Quinolinecarbonitrile,4-chloro-7-(trifluoromethyl)- (CAS: 157301-81-0) represents a promising scaffold in medicinal chemistry, with demonstrated applications in kinase inhibition and antimicrobial therapy. Recent advancements in synthetic methodologies and biological evaluations have further highlighted its potential. As research progresses, this compound is likely to play an increasingly important role in the development of novel therapeutic agents, addressing unmet medical needs in various disease areas.

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