Cas no 945896-79-7 (6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine)

6-Chloro-N-(4-fluorobenzyl)pyrimidin-4-amine is a fluorinated pyrimidine derivative with potential applications in pharmaceutical and agrochemical research. Its structure features a chloro-substituted pyrimidine core linked to a 4-fluorobenzylamine group, offering reactivity for further functionalization. The presence of both chloro and fluoro substituents enhances its utility as an intermediate in cross-coupling reactions, nucleophilic substitutions, or as a scaffold for bioactive molecule synthesis. The compound’s well-defined heterocyclic framework may contribute to binding affinity in medicinal chemistry applications, particularly in kinase inhibition or antimicrobial studies. Its purity and stability under standard conditions make it suitable for controlled synthetic processes. Further characterization data, including spectroscopic and crystallographic properties, may be required for specialized applications.
6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine structure
945896-79-7 structure
Product Name:6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine
CAS No:945896-79-7
MF:C11H9ClFN3
MW:237.660664319992
CID:3159931
PubChem ID:22309495
Update Time:2025-10-31

6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine Chemical and Physical Properties

Names and Identifiers

    • (6-Chloro-pyrimidin-4-yl)-(4-fluoro-benzyl)-amine
    • 945896-79-7
    • 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine
    • 6-chloro-N-[(4-fluorophenyl)methyl]pyrimidin-4-amine
    • AKOS009103818
    • CS-0367386
    • N-(4-fluorobenzyl)-6-chloropyrimidin-4-amine
    • F1967-4530
    • BP-20037
    • Inchi: 1S/C11H9ClFN3/c12-10-5-11(16-7-15-10)14-6-8-1-3-9(13)4-2-8/h1-5,7H,6H2,(H,14,15,16)
    • InChI Key: MYVPHLWTSQJTPS-UHFFFAOYSA-N
    • SMILES: ClC1=CC(=NC=N1)NCC1C=CC(=CC=1)F

Computed Properties

  • Exact Mass: 237.0469032Da
  • Monoisotopic Mass: 237.0469032Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 209
  • 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: 3.1
  • Topological Polar Surface Area: 37.8?2

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Additional information on 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine

Professional Introduction to Compound with CAS No. 945896-79-7 and Product Name: 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine

The compound with the CAS number 945896-79-7 and the product name 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine represents a significant advancement in the field of pharmaceutical chemistry. This pyrimidine derivative has garnered considerable attention due to its unique structural properties and promising biological activities. Pyrimidines are a class of heterocyclic aromatic organic compounds that are fundamental in the synthesis of nucleic acids, making them crucial in medicinal chemistry for the development of drugs targeting various diseases.

The molecular structure of 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine features a chloro substituent at the 6-position of the pyrimidine ring and a 4-fluorobenzyl group attached to the nitrogen atom at the 4-position. This specific arrangement of functional groups imparts distinct chemical and biological properties, making it a valuable scaffold for drug discovery. The chloro group enhances electrophilicity, facilitating further derivatization, while the fluorobenzyl moiety introduces hydrophobicity and potential metabolic stability.

Recent research has highlighted the therapeutic potential of 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine in several pharmacological contexts. Studies have demonstrated its efficacy as an inhibitor of enzymes involved in cancer cell proliferation. Specifically, it has shown promise in targeting kinases that are aberrantly activated in various malignancies. The fluorine atom in the benzyl group contributes to increased binding affinity by enhancing hydrophobic interactions with target proteins, a phenomenon known as "fluorine effect." This makes the compound an attractive candidate for developing kinase inhibitors with improved pharmacokinetic profiles.

In addition to its antineoplastic properties, preliminary investigations have explored the antimicrobial activity of 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine. The structural features of this compound exhibit interactions with bacterial enzymes, potentially disrupting essential metabolic pathways. Such findings are particularly relevant in light of the growing crisis of antibiotic resistance, where novel antimicrobial agents are urgently needed. The pyrimidine core is also known to interact with viral polymerases, suggesting further applications in antiviral therapies.

The synthesis of 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine involves multi-step organic reactions that showcase the ingenuity of synthetic chemists. Key steps include nucleophilic substitution reactions to introduce the chloro and fluorobenzyl groups, followed by cyclization to form the pyrimidine ring. Advanced techniques such as palladium-catalyzed cross-coupling reactions have been employed to achieve high regioselectivity and yield. These synthetic methodologies not only highlight the compound's accessibility but also demonstrate its versatility as a building block for more complex derivatives.

Biological evaluation of 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine has revealed intriguing interactions with cellular pathways relevant to inflammation and immune response. Preclinical studies indicate that this compound modulates signaling cascades involved in cytokine production, offering potential benefits in treating autoimmune disorders and chronic inflammatory conditions. The ability to fine-tune these pathways without excessive side effects is a critical factor in drug development, and 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine shows promise in achieving this balance.

The role of computational chemistry in optimizing 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine cannot be overstated. Molecular modeling techniques have been instrumental in predicting binding affinities and identifying optimal analogs for further development. By leveraging artificial intelligence-driven platforms, researchers can accelerate virtual screening processes, identifying lead compounds that exhibit enhanced potency and selectivity. This interdisciplinary approach merges traditional organic synthesis with cutting-edge computational methods, fostering innovation in drug discovery.

Future directions for research on 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine include exploring its role in precision medicine applications. Personalized treatment strategies require compounds that can be tailored to individual patient profiles, and this pyrimidine derivative offers flexibility for such adaptations. Additionally, investigating its interaction with other therapeutic agents may uncover synergistic effects that could improve treatment outcomes for multifaceted diseases.

In conclusion, 6-chloro-N-(4-fluorobenzyl)pyrimidin-4-amine (CAS No. 945896-79-7) stands as a testament to the relentless pursuit of novel pharmaceuticals driven by structural innovation and biological insight. Its unique chemical profile positions it as a versatile tool for addressing unmet medical needs across oncology, antimicrobial therapy, and immunomodulation. As research continues to unravel its full potential, this compound exemplifies how targeted molecular design can lead to breakthroughs with profound implications for human health.

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