Cas no 66573-61-3 (3-chloro-6-(3-fluorophenyl)pyridazine)

3-Chloro-6-(3-fluorophenyl)pyridazine is a halogenated pyridazine derivative with a fluorinated phenyl substituent, offering unique reactivity and structural features for synthetic applications. The presence of both chloro and fluoro functional groups enhances its utility as a versatile intermediate in pharmaceutical and agrochemical research, enabling selective modifications via nucleophilic substitution or cross-coupling reactions. Its electron-deficient pyridazine core and aromatic fluorination contribute to potential bioactivity, making it valuable in drug discovery for targeting specific receptors or enzymes. The compound’s well-defined structure and stability under standard conditions facilitate its use in method development and scale-up processes. Suitable for controlled functionalization, it serves as a key building block in heterocyclic chemistry.
3-chloro-6-(3-fluorophenyl)pyridazine structure
66573-61-3 structure
Product Name:3-chloro-6-(3-fluorophenyl)pyridazine
CAS No:66573-61-3
MF:C10H6ClFN2
MW:208.61944437027
MDL:MFCD12143146
CID:1115656
PubChem ID:12449556
Update Time:2025-05-24

3-chloro-6-(3-fluorophenyl)pyridazine Chemical and Physical Properties

Names and Identifiers

    • 3-chloro-6-(3-fluorophenyl)-Pyridazine
    • 3-chloro-6-(3-fluorophenyl)pyridazine
    • MFCD12143146
    • BS-3553
    • AKOS005207986
    • SCHEMBL11630165
    • SWHBEWAGUFMFCG-UHFFFAOYSA-N
    • 3-chloro-6-(m-fluorophenyl)pyridazine
    • 66573-61-3
    • EN300-236483
    • F1967-0397
    • CS-0454699
    • DB-379008
    • MDL: MFCD12143146
    • Inchi: 1S/C10H6ClFN2/c11-10-5-4-9(13-14-10)7-2-1-3-8(12)6-7/h1-6H
    • InChI Key: SWHBEWAGUFMFCG-UHFFFAOYSA-N
    • SMILES: ClC1=CC=C(C2C=CC=C(C=2)F)N=N1

Computed Properties

  • Exact Mass: 208.0203541g/mol
  • Monoisotopic Mass: 208.0203541g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 191
  • 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: 2.6
  • Topological Polar Surface Area: 25.8?2

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Additional information on 3-chloro-6-(3-fluorophenyl)pyridazine

Professional Introduction to 3-chloro-6-(3-fluorophenyl)pyridazine (CAS No: 66573-61-3)

3-chloro-6-(3-fluorophenyl)pyridazine, identified by the Chemical Abstracts Service Number (CAS No) 66573-61-3, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology. This compound belongs to the pyridazine class, characterized by a six-membered ring containing two nitrogen atoms. The presence of both a chlorine substituent at the 3-position and a 3-fluorophenyl group at the 6-position introduces unique electronic and steric properties, making it a promising candidate for further chemical and biological exploration.

The structural features of 3-chloro-6-(3-fluorophenyl)pyridazine contribute to its potential utility in drug discovery. The chlorine atom can serve as a handle for further functionalization via nucleophilic substitution reactions, while the fluorine atom in the phenyl ring enhances lipophilicity and metabolic stability, which are critical factors in medicinal chemistry. These attributes have positioned this compound as an attractive scaffold for developing novel therapeutic agents.

In recent years, there has been growing interest in pyridazine derivatives due to their diverse biological activities. Studies have demonstrated that pyridazine-based compounds exhibit a wide range of pharmacological effects, including antimicrobial, anti-inflammatory, and anticancer properties. The introduction of fluorine and chlorine substituents further modulates these activities, making 3-chloro-6-(3-fluorophenyl)pyridazine a subject of intense research.

One of the most compelling areas of investigation involves the antimicrobial applications of this compound. Research has shown that certain pyridazine derivatives can inhibit the growth of Gram-positive and Gram-negative bacteria by targeting essential bacterial enzymes. The structural motif of 3-chloro-6-(3-fluorophenyl)pyridazine is particularly noteworthy for its ability to disrupt bacterial cell wall synthesis and DNA replication. These findings suggest that this compound could be a valuable asset in the development of new antibiotics to combat drug-resistant bacterial strains.

Furthermore, the anticancer potential of 3-chloro-6-(3-fluorophenyl)pyridazine has been explored in several preclinical studies. Pyridazine derivatives have been identified as inhibitors of kinases and other enzymes involved in cancer cell proliferation. The fluorine atom in the phenyl ring enhances binding affinity to target proteins, improving the efficacy of the compound. Preliminary results indicate that 3-chloro-6-(3-fluorophenyl)pyridazine can induce apoptosis in various cancer cell lines while exhibiting minimal toxicity toward healthy cells. This selective toxicity makes it a promising candidate for further development into an anticancer therapeutic.

The synthesis of 3-chloro-6-(3-fluorophenyl)pyridazine involves multi-step organic reactions that require precise control over reaction conditions to ensure high yield and purity. Common synthetic routes include condensation reactions between halogenated pyridazines and fluorinated aromatic compounds, followed by chlorination to introduce the chlorine substituent at the 3-position. Advanced techniques such as transition metal-catalyzed cross-coupling reactions have also been employed to enhance synthetic efficiency.

The pharmacokinetic properties of 3-chloro-6-(3-fluorophenyl)pyridazine are another critical aspect that has been thoroughly investigated. In vitro studies have demonstrated that this compound exhibits good solubility in both aqueous and lipid environments, facilitating its absorption and distribution throughout the body. Additionally, its metabolic stability suggests that it could have a prolonged half-life, allowing for less frequent dosing in clinical applications.

Recent advancements in computational chemistry have enabled researchers to predict the biological activity of 3-chloro-6-(3-fluorophenyl)pyridazine with greater accuracy before conducting costly wet-lab experiments. Molecular docking simulations have identified potential binding pockets on target proteins, providing insights into how this compound interacts with biological systems. These computational approaches have significantly accelerated the drug discovery process by narrowing down promising candidates for further experimental validation.

The regulatory landscape for novel pharmaceutical compounds like 3-chloro-6-(3-fluorophenyl)pyridazine is stringent but well-established. Regulatory agencies require extensive preclinical and clinical data to support the safety and efficacy of new drugs before they can be approved for human use. Researchers must navigate complex regulatory pathways, including Good Manufacturing Practice (GMP) compliance and rigorous toxicological testing, to bring this compound from bench to market.

In conclusion, 3-chloro-6-(3-fluorophenyl)pyridazine (CAS No: 66573-61-3) represents a fascinating example of how structural modifications can enhance biological activity. Its potential applications in antimicrobial and anticancer therapies make it a compelling subject for further research. As our understanding of molecular interactions continues to evolve, compounds like this are poised to play a pivotal role in addressing some of the most pressing challenges in modern medicine.

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