Cas no 917251-92-4 (8-Bromo-5-(trifluoromethyl)quinoline)

8-Bromo-5-(trifluoromethyl)quinoline is a halogenated quinoline derivative featuring both bromine and trifluoromethyl functional groups, which enhance its reactivity and utility in synthetic chemistry. The bromine substituent facilitates further functionalization via cross-coupling reactions, while the electron-withdrawing trifluoromethyl group improves stability and influences electronic properties. This compound is particularly valuable in pharmaceutical and agrochemical research as a versatile intermediate for constructing complex heterocyclic frameworks. Its high purity and well-defined structure make it suitable for precision applications in medicinal chemistry and material science. The combination of halogen and fluorinated groups offers distinct advantages in tuning molecular interactions and metabolic stability.
8-Bromo-5-(trifluoromethyl)quinoline structure
917251-92-4 structure
Product Name:8-Bromo-5-(trifluoromethyl)quinoline
CAS No:917251-92-4
MF:C10H5BrF3N
MW:276.052612066269
MDL:MFCD11504935
CID:857467
PubChem ID:46739129
Update Time:2025-05-25

8-Bromo-5-(trifluoromethyl)quinoline Chemical and Physical Properties

Names and Identifiers

    • 8-Bromo-5-(trifluoromethyl)quinoline
    • 8-Bromo-5-trifluoromethylquinoline
    • SCHEMBL3628380
    • SLRQZPDPELUOEM-UHFFFAOYSA-N
    • BS-29803
    • MFCD11504935
    • DTXSID00674760
    • 917251-92-4
    • SB71684
    • CS-0197507
    • 8-bromo-5-trifluoromethylquinoline, AldrichCPR
    • SY280693
    • AT15553
    • EN300-6494904
    • AKOS015834736
    • 8-Bromo-5-(trifluoromethyl)quinoline (ACI)
    • MDL: MFCD11504935
    • Inchi: 1S/C10H5BrF3N/c11-8-4-3-7(10(12,13)14)6-2-1-5-15-9(6)8/h1-5H
    • InChI Key: SLRQZPDPELUOEM-UHFFFAOYSA-N
    • SMILES: BrC1=CC=C(C(F)(F)F)C2=CC=CN=C21

Computed Properties

  • Exact Mass: 274.95575g/mol
  • Monoisotopic Mass: 274.95575g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 231
  • 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: 3.9
  • Topological Polar Surface Area: 12.9?2

8-Bromo-5-(trifluoromethyl)quinoline Security Information

  • Hazard Category Code: 25-36
  • Safety Instruction: 26-45
  • Hazardous Material Identification: T

8-Bromo-5-(trifluoromethyl)quinoline Pricemore >>

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8-Bromo-5-(trifluoromethyl)quinoline Production Method

Production Method 1

Reaction Conditions
1.1 Catalysts: Sodium iodide ;  110 °C → 150 °C
1.2 Reagents: Sulfuric acid ;  150 °C; 1 h, 150 °C; 150 °C → rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized, rt
Reference
Auxiliary-Directed C(sp3)-H Arylation by Synergistic Photoredox and Palladium Catalysis
Czyz, Milena L. ; et al, Chemistry - A European Journal, 2017, 23(58), 14450-14453

Production Method 2

Reaction Conditions
1.1 Reagents: Methanesulfonic acid ,  Benzenesulfonic acid, 3-nitro-, sodium salt (1:1) Catalysts: Ferrous sulfate ;  20 h, 125 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  basified
Reference
Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts
Miyaji, Ryota; et al, Chemistry - A European Journal, 2017, 23(42), 9996-10000

8-Bromo-5-(trifluoromethyl)quinoline Raw materials

8-Bromo-5-(trifluoromethyl)quinoline Preparation Products

Additional information on 8-Bromo-5-(trifluoromethyl)quinoline

8-Bromo-5-(trifluoromethyl)quinoline: A Comprehensive Overview

8-Bromo-5-(trifluoromethyl)quinoline is a highly specialized organic compound with the CAS number 917251-92-4. This compound belongs to the quinoline family, which is a heterocyclic aromatic system with a nitrogen atom at position 1. The presence of a bromine atom at position 8 and a trifluoromethyl group at position 5 introduces unique electronic and structural properties, making it a valuable molecule in various fields of research and application.

The synthesis of 8-Bromo-5-(trifluoromethyl)quinoline involves advanced organic chemistry techniques, often requiring precise control over reaction conditions to achieve high yields and purity. Recent studies have focused on optimizing the synthesis pathways, leveraging catalytic methods and microwave-assisted reactions to enhance efficiency. These advancements have not only improved the scalability of production but also reduced environmental impact, aligning with current sustainability goals in chemical manufacturing.

One of the most promising applications of 8-Bromo-5-(trifluoromethyl)quinoline lies in the field of drug discovery. The compound has demonstrated significant potential as a lead molecule in the development of novel therapeutics targeting various diseases, including cancer and neurodegenerative disorders. Researchers have explored its ability to modulate key cellular pathways, such as kinase signaling and oxidative stress responses, which are critical in disease progression.

In addition to its therapeutic applications, 8-Bromo-5-(trifluoromethyl)quinoline has shown remarkable properties in materials science. Its unique electronic structure makes it an ideal candidate for use in organic electronics, particularly in the development of light-emitting diodes (LEDs) and photovoltaic devices. Recent studies have highlighted its ability to act as an efficient electron transporter, significantly improving device performance and stability.

The compound's stability under various environmental conditions has also made it a valuable tool in analytical chemistry. It is frequently used as a reference standard in spectroscopic analyses due to its well-defined spectral characteristics. Furthermore, its resistance to photodegradation makes it suitable for long-term storage and use in demanding experimental setups.

Recent advancements in computational chemistry have provided deeper insights into the molecular behavior of 8-Bromo-5-(trifluoromethyl)quinoline. Quantum mechanical simulations have revealed its electronic distribution patterns, which are crucial for understanding its reactivity and interaction with biological systems. These findings have paved the way for more targeted modifications of the molecule to enhance its desired properties.

In conclusion, 8-Bromo-5-(trifluoromethyl)quinoline is a versatile compound with a wide range of applications across multiple disciplines. Its unique chemical structure, combined with recent research breakthroughs, positions it as a key player in advancing scientific innovation. As ongoing studies continue to uncover new potential uses, this compound is poised to make significant contributions to both academic research and industrial applications.

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