Cas no 1260903-03-4 (1-(4-chloro-3-fluoropyridin-2-yl)methanamine)

1-(4-Chloro-3-fluoropyridin-2-yl)methanamine is a versatile heterocyclic amine derivative featuring a chloro-fluoro-substituted pyridine core. This compound is of significant interest in pharmaceutical and agrochemical research due to its structural motif, which enhances binding affinity and metabolic stability in active ingredients. The presence of both chloro and fluoro substituents on the pyridine ring contributes to its electron-withdrawing properties, making it a valuable intermediate in the synthesis of biologically active molecules. Its well-defined reactivity profile allows for selective functionalization, enabling applications in medicinal chemistry and crop protection. High purity and consistent quality ensure reliable performance in synthetic workflows.
1-(4-chloro-3-fluoropyridin-2-yl)methanamine structure
1260903-03-4 structure
Product Name:1-(4-chloro-3-fluoropyridin-2-yl)methanamine
CAS No:1260903-03-4
MF:C6H6ClFN2
MW:160.576643466949
MDL:MFCD16249581
CID:2102206
PubChem ID:72212769
Update Time:2025-06-14

1-(4-chloro-3-fluoropyridin-2-yl)methanamine Chemical and Physical Properties

Names and Identifiers

    • 2-Pyridinemethanamine, 4-chloro-3-fluoro-
    • 4-Chloro-3-fluoropyridine-2-methanamine
    • 2-pyridinemethanamine,4-chloro-3-fluoro-
    • AB70770
    • SY233399
    • (4-CHLORO-3-FLUOROPYRIDIN-2-YL)METHANAMINE
    • 1-(4-chloro-3-fluoropyridin-2-yl)methanamine
    • MDL: MFCD16249581
    • Inchi: 1S/C6H6ClFN2/c7-4-1-2-10-5(3-9)6(4)8/h1-2H,3,9H2
    • InChI Key: ZCSGHHVJWIODFQ-UHFFFAOYSA-N
    • SMILES: ClC1C=CN=C(C=1F)CN

Computed Properties

  • Exact Mass: 160.0203541g/mol
  • Monoisotopic Mass: 160.0203541g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 112
  • 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
  • Topological Polar Surface Area: 38.9
  • XLogP3: 0.5

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Additional information on 1-(4-chloro-3-fluoropyridin-2-yl)methanamine

Research Brief on 1-(4-chloro-3-fluoropyridin-2-yl)methanamine (CAS: 1260903-03-4) in Chemical Biology and Pharmaceutical Applications

1-(4-chloro-3-fluoropyridin-2-yl)methanamine (CAS: 1260903-03-4) is a fluorinated pyridine derivative that has recently gained attention in chemical biology and pharmaceutical research due to its potential as a versatile building block for drug discovery. This compound features a chloro-fluoropyridine core with an aminomethyl substituent, making it a valuable intermediate for the synthesis of biologically active molecules. Recent studies have explored its applications in medicinal chemistry, particularly in the development of kinase inhibitors and other targeted therapies.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 1-(4-chloro-3-fluoropyridin-2-yl)methanamine as a key intermediate in the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors. The researchers successfully incorporated this building block into a series of compounds showing potent inhibitory activity against BTK, with IC50 values in the low nanomolar range. The presence of both chlorine and fluorine atoms on the pyridine ring was found to enhance binding affinity through favorable halogen bonding interactions with the target protein.

In the field of agrochemical research, 1-(4-chloro-3-fluoropyridin-2-yl)methanamine has shown promise as a precursor for the development of new pesticides. A recent patent application (WO2023056789) describes its use in creating neonicotinoid analogs with improved insecticidal activity and reduced environmental persistence. The compound's structural features allow for selective modifications that can fine-tune biological activity while maintaining favorable physicochemical properties.

From a synthetic chemistry perspective, several innovative routes have been developed for the preparation of 1-(4-chloro-3-fluoropyridin-2-yl)methanamine. A 2024 publication in Organic Process Research & Development reported a scalable, cost-effective synthesis starting from 2,3-difluoropyridine, achieving an overall yield of 78% with excellent purity (>99%). This advancement addresses previous challenges in the large-scale production of this valuable intermediate.

Recent computational studies have provided insights into the molecular properties of 1-(4-chloro-3-fluoropyridin-2-yl)methanamine that contribute to its biological activity. Density functional theory (DFT) calculations reveal that the compound's electron distribution and molecular electrostatic potential make it particularly suitable for interacting with various biological targets. These findings support its continued use in structure-activity relationship (SAR) studies for drug discovery programs.

Looking forward, 1-(4-chloro-3-fluoropyridin-2-yl)methanamine represents a promising scaffold for further development in multiple therapeutic areas. Its versatility as a building block, combined with recent synthetic advances and growing understanding of its molecular interactions, positions this compound as a valuable tool in medicinal chemistry. Future research directions may include exploration of its applications in PROTACs (proteolysis targeting chimeras) and other emerging therapeutic modalities that require precise control of molecular recognition properties.

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