Cas no 1449008-17-6 (2,5-Dichloro-1-methylpyridin-4(1H)-one)

2,5-Dichloro-1-methylpyridin-4(1H)-one is a chlorinated pyridinone derivative with significant utility in synthetic organic chemistry. Its structure features a 1-methyl-4-pyridinone core substituted with chlorine atoms at the 2- and 5-positions, enhancing its reactivity as an intermediate for further functionalization. This compound exhibits notable stability under standard conditions, making it suitable for diverse transformations, including nucleophilic substitutions and cross-coupling reactions. Its electron-deficient pyridinone ring system is particularly valuable in the synthesis of heterocyclic compounds and pharmaceutical scaffolds. The presence of two chlorine atoms offers selective reactivity for stepwise modifications, while the methyl group at the 1-position improves solubility in organic solvents. This combination of features makes it a versatile building block for medicinal chemistry and material science applications.
2,5-Dichloro-1-methylpyridin-4(1H)-one structure
1449008-17-6 structure
Product Name:2,5-Dichloro-1-methylpyridin-4(1H)-one
CAS No:1449008-17-6
MF:C6H5Cl2NO
MW:178.0160
MDL:MFCD24848705
CID:2093793
PubChem ID:74890481
Update Time:2025-07-02

2,5-Dichloro-1-methylpyridin-4(1H)-one Chemical and Physical Properties

Names and Identifiers

    • 2,5-Dichloro-1-methylpyridin-4(1H)-one
    • 2,5-Dichloro-1-methyl-3,6-2H-pyridin-4-one
    • AK167711
    • 2,5-dichloro-1-methylpyridin-4-one
    • FCH2346980
    • 2,5-Dichloro-1-methyl-4(1H)-pyridinone
    • Z1275
    • C72747
    • MFCD24848705
    • 4(1H)-Pyridinone, 2,5-dichloro-1-methyl-
    • AB92991
    • SY111376
    • ZHC00817
    • AKOS025287419
    • DS-9556
    • 1449008-17-6
    • DB-121871
    • AC-33336
    • CS-0151193
    • MDL: MFCD24848705
    • Inchi: 1S/C6H5Cl2NO/c1-9-3-4(7)5(10)2-6(9)8/h2-3H,1H3
    • InChI Key: ADFFJPJHMUFPRW-UHFFFAOYSA-N
    • SMILES: ClC1=C([H])C(C(=C([H])N1C([H])([H])[H])Cl)=O

Computed Properties

  • Exact Mass: 176.9748192g/mol
  • Monoisotopic Mass: 176.9748192g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 232
  • 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: 20.3
  • XLogP3: 2

2,5-Dichloro-1-methylpyridin-4(1H)-one Pricemore >>

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Additional information on 2,5-Dichloro-1-methylpyridin-4(1H)-one

2,5-Dichloro-1-methylpyridin-4(1H)-one: A Comprehensive Overview of Its Chemical Properties and Applications

2,5-Dichloro-1-methylpyridin-4(1H)-one is a synthetic compound with the chemical formula C7H5Cl2NO. This molecule belongs to the class of pyridinone derivatives, which are known for their diverse biological activities and potential applications in pharmaceutical research. The CAS No. 1449008-17-6 serves as a unique identifier for this compound, enabling precise referencing in scientific literature and industrial applications. The structural features of this compound, including the presence of two chlorine atoms at the 2- and 5-positions of the pyridine ring and a methyl group at the 1-position, contribute to its distinct chemical behavior and functional properties.

Recent studies have highlighted the significance of 2,5-Dichloro-1-methylpyridin-3(2H)-one as a key intermediate in the synthesis of various bioactive molecules. Researchers have demonstrated that the chlorinated substituents on the pyridine ring enhance the molecule's ability to interact with specific biological targets, such as enzymes and receptors. This unique structural configuration allows the compound to exhibit selective biological activities, making it a promising candidate for further exploration in drug discovery. The pyridinone ring is a well-known pharmacophore in medicinal chemistry, and the introduction of chlorine atoms at specific positions can modulate its reactivity and binding affinity.

One of the most recent breakthroughs in the study of 2,5-Dichloro-1-methylpyridin-4(1H)-one involves its role in the development of novel antimicrobial agents. A 2023 study published in the Journal of Medicinal Chemistry reported that this compound demonstrates potent activity against multidrug-resistant bacterial strains. The mechanism of action appears to involve the disruption of bacterial cell membrane integrity, as supported by molecular docking studies. This finding underscores the potential of 2,5-Dichloro-1-methylpyridin-4(1H)-one as a lead compound for the design of new antibiotics, addressing the growing global challenge of antibiotic resistance.

Another area of interest is the application of 2,5-Dichloro-1-methylpyridin-4(1H)-one in the field of cancer research. Preliminary studies suggest that this compound may exhibit antitumor properties by targeting specific signaling pathways involved in cell proliferation and apoptosis. A 2022 study published in Cancer Research demonstrated that 2,5-Dichloro-1-methylpyridin-4(1H)-one can inhibit the activity of certain kinases associated with tumor progression. These findings highlight the potential of this compound as a therapeutic agent for the treatment of specific cancers, although further clinical trials are needed to validate its efficacy and safety.

The synthesis of 2,5-Dichloro-1-methylpyridin-4(1H)-one has been optimized in recent years to improve its yield and purity. One notable method involves the chlorination of 1-methylpyridin-4(1H)-one using a combination of chlorine gas and a suitable catalyst. This process allows for the selective introduction of chlorine atoms at the 2- and 5-positions of the pyridine ring, which is critical for achieving the desired biological activity. Researchers have also explored the use of microwave-assisted synthesis to enhance the efficiency of this reaction, reducing both reaction time and energy consumption.

From a pharmacological perspective, the pyridinone ring in 2,5-Dichloro-1-methylpyridin-4(1H)-one is believed to play a key role in its biological activity. The presence of chlorine atoms at specific positions may influence the molecule's ability to bind to target proteins, such as enzymes or receptors. This hypothesis is supported by computational studies that have modeled the interactions between 2,5-Dichloro-1-methylpyridin-4(1H)-one and various biological targets. These studies suggest that the chlorinated substituents can enhance the molecule's affinity for certain proteins, thereby improving its therapeutic potential.

Despite its promising properties, the use of 2,5-Dichloro-1-methylpyridin-4(1H)-one is not without challenges. One of the main concerns is its potential toxicity, which requires further investigation to ensure its safety for therapeutic applications. Researchers are currently exploring ways to modify the structure of this compound to reduce its toxicity while maintaining its biological activity. This includes the introduction of functional groups that can alter the molecule's reactivity and improve its pharmacokinetic profile.

In conclusion, 2,5-Dichloro-1-methylpyridin-4(1H)-one represents an important molecule in the field of medicinal chemistry. Its unique structural features and potential biological activities make it a valuable candidate for further research and development. As new studies continue to emerge, the role of this compound in drug discovery and therapeutic applications is likely to expand, offering new possibilities for the treatment of various diseases.

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