Cas no 402561-66-4 (1-(3,5-Dichloropyridin-4-yl)ethan-1-one)

1-(3,5-Dichloropyridin-4-yl)ethan-1-one is a chlorinated pyridine derivative with a ketone functional group, serving as a versatile intermediate in organic synthesis. Its structure features dichloro-substitution at the 3- and 5-positions of the pyridine ring, enhancing reactivity for further functionalization. This compound is particularly valuable in pharmaceutical and agrochemical research due to its ability to act as a precursor for heterocyclic compounds. The electron-withdrawing effects of the chlorine substituents improve its stability while maintaining reactivity in nucleophilic substitution and cross-coupling reactions. Its high purity and well-defined structure make it suitable for precise synthetic applications.
1-(3,5-Dichloropyridin-4-yl)ethan-1-one structure
402561-66-4 structure
Product Name:1-(3,5-Dichloropyridin-4-yl)ethan-1-one
CAS No:402561-66-4
MF:C7H5Cl2NO
MW:190.026699781418
MDL:MFCD11847308
CID:822968
PubChem ID:15531549
Update Time:2025-10-08

1-(3,5-Dichloropyridin-4-yl)ethan-1-one Chemical and Physical Properties

Names and Identifiers

    • 1-(3,5-Dichloropyridin-4-yl)ethan-1-one
    • 1-(3,5-dichloropyridin-4-yl)ethanone
    • AS-62755
    • AKOS022176066
    • DTXSID90573733
    • 1-(3,5-Dichloro-4-pyridinyl)ethanone
    • SCHEMBL1286681
    • 1-(3,5dichloropyridin-4-yl)ethanone
    • CRA56166
    • Ethanone, 1-(3,5-dichloro-4-pyridinyl)-
    • DB-087051
    • MFCD11847308
    • FD10663
    • CS-0193995
    • 402561-66-4
    • 1-(3,5-Dichloropyridin-4-yl)ethanone;1-(3,5-Dichloropyridin-4-yl)ethan-1-one
    • MDL: MFCD11847308
    • Inchi: 1S/C7H5Cl2NO/c1-4(11)7-5(8)2-10-3-6(7)9/h2-3H,1H3
    • InChI Key: AWJCMJFTASVFIB-UHFFFAOYSA-N
    • SMILES: ClC1C=NC=C(C=1C(C)=O)Cl

Computed Properties

  • Exact Mass: 188.9748192g/mol
  • Monoisotopic Mass: 188.9748192g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 153
  • 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: 1.8
  • Topological Polar Surface Area: 30?2

Experimental Properties

  • Density: 1.376±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 210.5±35.0 oC (760 Torr),
  • Flash Point: 81.1±25.9 oC,
  • Solubility: Slightly soluble (1.3 g/l) (25 o C),

1-(3,5-Dichloropyridin-4-yl)ethan-1-one Security Information

  • Hazard Category Code: 22-36
  • Safety Instruction: 26
  • Hazardous Material Identification: Xn

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Additional information on 1-(3,5-Dichloropyridin-4-yl)ethan-1-one

Introduction to 1-(3,5-Dichloropyridin-4-yl)ethan-1-one (CAS No. 402561-66-4)

1-(3,5-Dichloropyridin-4-yl)ethan-1-one, also known by its CAS number 402561-66-4, is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is characterized by its unique structure, which includes a dichloropyridine moiety and an acetone-like ketone group. These structural features contribute to its potential applications in various biological and therapeutic contexts.

The chemical formula of 1-(3,5-Dichloropyridin-4-yl)ethan-1-one is C8H5Cl2N2O, and it has a molecular weight of approximately 208.04 g/mol. The compound is a white crystalline solid at room temperature and is soluble in common organic solvents such as dimethyl sulfoxide (DMSO), methanol, and ethanol. Its physical and chemical properties make it suitable for use in a wide range of experimental conditions.

In recent years, 1-(3,5-Dichloropyridin-4-yl)ethan-1-one has been extensively studied for its potential as a lead compound in drug discovery. One of the key areas of interest is its role as an inhibitor of specific enzymes and receptors. For instance, research has shown that this compound can act as a potent inhibitor of the enzyme PDE4 (Phosphodiesterase 4), which is involved in the regulation of cyclic adenosine monophosphate (cAMP) levels in cells. PDE4 inhibitors have been explored for their anti-inflammatory and anti-depressant properties, making them promising candidates for the treatment of conditions such as chronic obstructive pulmonary disease (COPD) and major depressive disorder (MDD).

Beyond its enzymatic inhibition properties, 1-(3,5-Dichloropyridin-4-yl)ethan-1-one has also been investigated for its potential as an antiviral agent. Studies have demonstrated that this compound can effectively inhibit the replication of certain viruses, including influenza A virus and human immunodeficiency virus (HIV). The mechanism by which it exerts these antiviral effects is not yet fully understood but is believed to involve the modulation of viral entry or replication processes within host cells.

The pharmacological profile of 1-(3,5-Dichloropyridin-4-yl)ethan-1-one has been further elucidated through various preclinical studies. In vitro assays have shown that it exhibits low cytotoxicity against mammalian cells, suggesting that it may have a favorable safety profile for therapeutic use. Additionally, animal models have been used to evaluate its pharmacokinetic properties, including absorption, distribution, metabolism, and excretion (ADME). These studies have indicated that the compound has good oral bioavailability and a reasonable half-life, making it suitable for further development as a potential drug candidate.

In the context of drug development, the synthesis and optimization of 1-(3,5-Dichloropyridin-4-yl)ethan-1-one-based compounds have been a focus of ongoing research. Chemists have explored various synthetic routes to produce this compound efficiently and cost-effectively. One common approach involves the reaction of 3,5-dichloroisonicotinic acid with acetone in the presence of a suitable catalyst. This method has been optimized to achieve high yields and purity levels, facilitating large-scale production for preclinical and clinical studies.

The structural modifications of 1-(3,5-Dichloropyridin-4-yl)ethan-1-one have also been investigated to enhance its biological activity and improve its pharmacological properties. For example, substituents on the pyridine ring or modifications to the ketone group can significantly affect the compound's binding affinity to target proteins or receptors. These efforts aim to identify more potent and selective derivatives that can be advanced into clinical trials.

Clinical trials involving compounds derived from 1-(3,5-Dichloropyridin-4-yl)ethan-1-one are currently underway to evaluate their safety and efficacy in human subjects. Early-phase trials have shown promising results, with some compounds demonstrating significant therapeutic benefits without major adverse effects. These findings underscore the potential of this class of compounds as novel therapeutic agents for various diseases.

In conclusion, 1-(3,5-Dichloropyridin-4-yl)ethan-1-one (CAS No. 402561-66-4) is a promising compound with diverse applications in medicinal chemistry and pharmaceutical research. Its unique structural features and favorable biological properties make it an attractive candidate for further development as a therapeutic agent. Ongoing research continues to uncover new insights into its mechanisms of action and potential therapeutic uses, paving the way for innovative treatments in the future.

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