Cas no 1156275-50-1 (8-bromo-4-chloro-6-methyl-2-phenylquinoline)

8-Bromo-4-chloro-6-methyl-2-phenylquinoline is a halogenated quinoline derivative with a molecular formula of C??H??BrClN. This compound features a bromo substituent at the 8-position, a chloro group at the 4-position, and a methyl group at the 6-position, along with a phenyl ring at the 2-position. Its structural modifications enhance its utility as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. The electron-withdrawing halogen atoms improve reactivity in cross-coupling reactions, while the phenyl and methyl groups contribute to steric and electronic tuning. This compound is valued for its stability, well-defined reactivity, and potential applications in medicinal chemistry research.
8-bromo-4-chloro-6-methyl-2-phenylquinoline structure
1156275-50-1 structure
Product Name:8-bromo-4-chloro-6-methyl-2-phenylquinoline
CAS No:1156275-50-1
MF:C16H11BrClN
MW:332.622242212296
CID:1205013
PubChem ID:43668594
Update Time:2025-10-28

8-bromo-4-chloro-6-methyl-2-phenylquinoline Chemical and Physical Properties

Names and Identifiers

    • 8-bromo-4-chloro-6-methyl-2-phenylquinoline
    • CTK8E5557
    • ZINC36075702
    • AKOS009867694
    • CTK8E5557; ZINC36075702; AKOS009867694;
    • MFCD12592126
    • 1156275-50-1
    • DTXSID00656309
    • Inchi: 1S/C16H11BrClN/c1-10-7-12-14(18)9-15(11-5-3-2-4-6-11)19-16(12)13(17)8-10/h2-9H,1H3
    • InChI Key: BBAQZDIOXQIUEF-UHFFFAOYSA-N
    • SMILES: BrC1=CC(C)=CC2=C(C=C(C3C=CC=CC=3)N=C21)Cl

Computed Properties

  • Exact Mass: 330.97600
  • Monoisotopic Mass: 330.97634g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 1
  • Complexity: 305
  • 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: 5.5
  • Topological Polar Surface Area: 12.9?2

Experimental Properties

  • PSA: 12.89000
  • LogP: 5.62610

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Additional information on 8-bromo-4-chloro-6-methyl-2-phenylquinoline

Introduction to 8-bromo-4-chloro-6-methyl-2-phenylquinoline (CAS No. 1156275-50-1)

8-bromo-4-chloro-6-methyl-2-phenylquinoline, identified by its Chemical Abstracts Service (CAS) number 1156275-50-1, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the quinoline family, a class of molecules known for their broad spectrum of biological activities and utility in drug development. The structural features of this molecule, including its bromo, chloro, and methyl substituents, as well as its phenyl group, contribute to its unique chemical properties and potential applications.

The quinoline scaffold is a privileged structure in medicinal chemistry, with numerous derivatives exhibiting antimicrobial, antimalarial, anti-inflammatory, and anticancer properties. Among these derivatives, 8-bromo-4-chloro-6-methyl-2-phenylquinoline stands out due to its modified substituents, which may enhance its binding affinity to biological targets and improve its pharmacokinetic profile. The presence of bromine and chlorine atoms introduces electrophilic centers that can participate in various chemical reactions, making this compound a valuable intermediate in synthetic chemistry.

In recent years, there has been a surge in research focused on developing novel quinoline-based compounds with enhanced therapeutic efficacy and reduced side effects. The modifications introduced in 8-bromo-4-chloro-6-methyl-2-phenylquinoline are designed to optimize its interaction with biological targets while minimizing toxicity. For instance, the bromo and chloro substituents can increase the lipophilicity of the molecule, facilitating its penetration across biological membranes. Additionally, the methyl group at the 6-position may stabilize the molecule’s three-dimensional structure, improving its binding stability to protein targets.

One of the most compelling aspects of 8-bromo-4-chloro-6-methyl-2-phenylquinoline is its potential application in the development of targeted therapies for cancer. Quinoline derivatives have shown promise in inhibiting kinases and other enzymes involved in tumor growth and progression. The structural features of this compound make it a candidate for further exploration as an inhibitor of specific cancer-related pathways. Preclinical studies have demonstrated that quinoline-based compounds can induce apoptosis in cancer cells by disrupting key signaling cascades.

Furthermore, 8-bromo-4-chloro-6-methyl-2-phenylquinoline has been investigated for its antimicrobial properties. The quinoline scaffold is well-known for its activity against a wide range of bacterial and parasitic infections. The introduction of halogen atoms into the molecule may enhance its ability to disrupt microbial cell membranes or inhibit essential metabolic processes. This makes it a promising candidate for developing new antibiotics or antiparasitic drugs to combat resistant strains.

The synthesis of 8-bromo-4-chloro-6-methyl-2-phenylquinoline involves multi-step organic reactions that require careful optimization to ensure high yield and purity. The bromination and chlorination steps are particularly critical, as they determine the reactivity and selectivity of the compound. Advanced synthetic techniques such as palladium-catalyzed cross-coupling reactions have been employed to introduce the phenyl group efficiently. These methods not only improve the efficiency of synthesis but also minimize byproduct formation, making the process more sustainable.

Recent advances in computational chemistry have also played a significant role in understanding the pharmacological properties of 8-bromo-4-chloro-6-methyl-2-phenylquinoline. Molecular docking studies have been used to predict how this compound interacts with various biological targets, including protein kinases and transcription factors. These simulations provide valuable insights into the binding mechanism and help guide further structural optimization efforts.

The pharmacokinetic profile of 8-bromo-4-chloro-6-methyl-2-phenylquinoline is another area of active research. Understanding how quickly the compound is absorbed, distributed, metabolized, and excreted (ADME) is crucial for determining its therapeutic potential. In vitro studies have shown that this compound exhibits moderate solubility in water and lipids, suggesting it may have good oral bioavailability. However, further studies are needed to assess its metabolic stability and potential for drug-drug interactions.

In conclusion,8-bromo-4-chloro--methyl--2--phenylquinoline (CAS No 11562--75--50--1) is a promising pharmacological agent with diverse therapeutic applications. Its unique structural features make it a valuable tool for further research in oncology antimicrobial drug development The ongoing studies on this compound highlight its potential as a lead molecule for novel therapeutics targeting cancer microbial infections

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