Cas no 1267009-84-6 (2-Chloro-5-(2-methoxyphenyl)pyrimidine)

2-Chloro-5-(2-methoxyphenyl)pyrimidine is a versatile heterocyclic compound featuring a pyrimidine core substituted with a chloro group at the 2-position and a 2-methoxyphenyl moiety at the 5-position. This structure imparts reactivity suitable for further functionalization, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The chloro group facilitates nucleophilic substitution reactions, while the methoxyphenyl substituent enhances electronic diversity, enabling applications in cross-coupling and cyclization reactions. Its well-defined molecular architecture ensures consistent performance in medicinal chemistry research, particularly in the development of kinase inhibitors and other biologically active compounds. The compound is typically supplied with high purity, ensuring reliability in synthetic workflows.
2-Chloro-5-(2-methoxyphenyl)pyrimidine structure
1267009-84-6 structure
Product Name:2-Chloro-5-(2-methoxyphenyl)pyrimidine
CAS No:1267009-84-6
MF:C11H9ClN2O
MW:220.65496134758
MDL:MFCD19318522
CID:4781418
Update Time:2026-02-27

2-Chloro-5-(2-methoxyphenyl)pyrimidine Chemical and Physical Properties

Names and Identifiers

    • 2-Chloro-5-(2-methoxyphenyl)pyrimidine
    • MDL: MFCD19318522
    • Inchi: 1S/C11H9ClN2O/c1-15-10-5-3-2-4-9(10)8-6-13-11(12)14-7-8/h2-7H,1H3
    • InChI Key: SRKXHHJHLQPWMT-UHFFFAOYSA-N
    • SMILES: ClC1=NC=C(C=N1)C1C=CC=CC=1OC

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 195
  • XLogP3: 2.8
  • Topological Polar Surface Area: 35

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Additional information on 2-Chloro-5-(2-methoxyphenyl)pyrimidine

Recent Advances in the Study of 2-Chloro-5-(2-methoxyphenyl)pyrimidine (CAS: 1267009-84-6) in Chemical Biology and Pharmaceutical Research

The compound 2-Chloro-5-(2-methoxyphenyl)pyrimidine (CAS: 1267009-84-6) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This heterocyclic compound, characterized by its pyrimidine core substituted with a chloro group at the 2-position and a 2-methoxyphenyl group at the 5-position, has demonstrated promising potential in various therapeutic applications. Recent studies have explored its role as a key intermediate in the synthesis of bioactive molecules and its direct pharmacological effects, particularly in the context of kinase inhibition and anticancer activity.

One of the most notable advancements in the study of 2-Chloro-5-(2-methoxyphenyl)pyrimidine is its application in the development of kinase inhibitors. Kinases are critical regulators of cellular signaling pathways, and their dysregulation is often implicated in cancer and other diseases. Researchers have utilized this compound as a scaffold to design novel inhibitors targeting specific kinases, such as EGFR (Epidermal Growth Factor Receptor) and VEGFR (Vascular Endothelial Growth Factor Receptor). The chloro and methoxyphenyl substituents provide strategic points for further chemical modifications, enabling the optimization of binding affinity and selectivity.

In a recent study published in the Journal of Medicinal Chemistry, a team of researchers synthesized a series of derivatives based on 2-Chloro-5-(2-methoxyphenyl)pyrimidine and evaluated their inhibitory activity against a panel of kinases. The results revealed that certain derivatives exhibited potent inhibition of EGFR with IC50 values in the nanomolar range. Molecular docking studies further elucidated the binding interactions, highlighting the importance of the chloro group in forming halogen bonds with key residues in the kinase active site.

Beyond its role in kinase inhibition, 2-Chloro-5-(2-methoxyphenyl)pyrimidine has also been investigated for its potential as an anticancer agent. Preclinical studies have demonstrated that this compound can induce apoptosis in cancer cell lines by modulating the expression of pro-apoptotic and anti-apoptotic proteins. For instance, in a study conducted on breast cancer cell lines, treatment with 2-Chloro-5-(2-methoxyphenyl)pyrimidine led to a significant reduction in cell viability and an increase in caspase-3 activity, a marker of apoptosis. These findings suggest that the compound may serve as a promising lead for the development of new anticancer therapies.

The synthetic versatility of 2-Chloro-5-(2-methoxyphenyl)pyrimidine has also been a focal point of recent research. Its reactivity allows for diverse functionalization, making it a valuable building block in medicinal chemistry. For example, the chloro group can be readily displaced via nucleophilic aromatic substitution, enabling the introduction of various amine or thiol substituents. This flexibility has been exploited to create libraries of compounds for high-throughput screening, accelerating the discovery of new drug candidates.

Despite these promising developments, challenges remain in the clinical translation of 2-Chloro-5-(2-methoxyphenyl)pyrimidine-based therapies. Issues such as bioavailability, metabolic stability, and potential off-target effects need to be addressed through further optimization and preclinical testing. Nevertheless, the compound's unique chemical properties and biological activities position it as a valuable tool for both basic research and drug development.

In conclusion, 2-Chloro-5-(2-methoxyphenyl)pyrimidine (CAS: 1267009-84-6) represents a versatile and pharmacologically relevant scaffold in modern chemical biology and pharmaceutical research. Recent studies have underscored its potential in kinase inhibition, anticancer therapy, and synthetic chemistry, paving the way for future innovations in drug discovery. Continued exploration of this compound and its derivatives is likely to yield significant advancements in the treatment of various diseases, particularly cancer.

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