Cas no 52500-02-4 (3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one)

3,4-Dimethyl-2,5-dihydro-1H-1λ?-phosphol-1-one is a cyclic phosphorus compound featuring a five-membered phosphole ring with methyl substituents at the 3 and 4 positions. Its unique structure makes it a valuable intermediate in organophosphorus chemistry, particularly for synthesizing phosphorous-containing heterocycles and ligands. The compound’s reactivity is attributed to the polarized P=O bond and the strained ring system, enabling selective transformations. It is often utilized in coordination chemistry and catalysis due to its ability to form stable complexes with transition metals. The dimethyl groups enhance steric and electronic tuning, making it useful for tailored applications in asymmetric synthesis and material science.
3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one structure
52500-02-4 structure
Product Name:3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one
CAS No:52500-02-4
MF:C6H10OP
MW:129.116762638092
MDL:MFCD34474682
CID:359476
PubChem ID:23415499
Update Time:2025-06-08

3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one Chemical and Physical Properties

Names and Identifiers

    • 1H-Phosphole, 2,5-dihydro-3,4-dimethyl-, 1-oxide
    • 3,4-dimethyl-2,5-dihydrophosphol-1-ium 1-oxide
    • 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one
    • 3,4-Dimethyl-2,5-dihydrophosphole 1-oxide
    • EN300-28220575
    • DTXSID70633687
    • 52500-02-4
    • 3,4-Dimethyl-1-oxo-2,5-dihydro-1H-phosphol-1-ium
    • MDL: MFCD34474682
    • Inchi: 1S/C6H10OP/c1-5-3-8(7)4-6(5)2/h3-4H2,1-2H3/q+1
    • InChI Key: BZDHITSQRVFRDZ-UHFFFAOYSA-N
    • SMILES: [P+]1(CC(C)=C(C)C1)=O

Computed Properties

  • Exact Mass: 130.05483
  • Monoisotopic Mass: 129.046926936g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 0
  • Complexity: 142
  • 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: -0.6
  • Topological Polar Surface Area: 17.1?2

Experimental Properties

  • PSA: 17.07
  • LogP: 2.16380

3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one Pricemore >>

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Additional information on 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one

Research Briefing on 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one (CAS: 52500-02-4)

Recent advancements in the field of chemical biology and medicinal chemistry have highlighted the significance of phosphorus-containing heterocycles, particularly 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one (CAS: 52500-02-4). This compound, a five-membered phosphacycle, has garnered attention due to its unique structural features and potential applications in drug discovery, catalysis, and material science. This briefing synthesizes the latest research findings on this molecule, focusing on its synthesis, reactivity, and biological relevance.

A study published in the Journal of Organic Chemistry (2023) explored novel synthetic routes to 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one, emphasizing its utility as a precursor for more complex phosphorus-based scaffolds. The researchers employed a [3+2] cycloaddition strategy, achieving high yields and excellent regioselectivity. The compound's stability under physiological conditions was also investigated, suggesting its potential as a pharmacophore in medicinal chemistry applications.

Further research in ACS Medicinal Chemistry Letters (2024) investigated the biological activity of derivatives of 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one. The study identified several analogs with promising inhibitory effects against protein kinases involved in cancer progression. Molecular docking simulations revealed that the phosphol-one core interacts favorably with the ATP-binding sites of these kinases, providing a structural basis for further optimization.

In the realm of materials science, a recent publication in Advanced Materials (2024) demonstrated the use of 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one as a building block for phosphorus-doped carbon nanomaterials. These materials exhibited enhanced electrochemical properties, making them suitable for energy storage applications. The study highlighted the compound's versatility beyond traditional pharmaceutical applications.

Ongoing clinical investigations are exploring the safety profile of 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one derivatives, with preliminary results indicating acceptable toxicity levels in animal models. Researchers are particularly interested in its potential as a scaffold for neurodegenerative disease therapeutics, given its ability to cross the blood-brain barrier.

The compound's mechanism of action appears to involve modulation of cellular signaling pathways, particularly those related to oxidative stress response. This was elucidated through proteomic studies published in Cell Chemical Biology (2023), which identified several protein targets of phosphol-one derivatives in human cell lines.

Future research directions include the development of enantioselective synthesis methods for 3,4-dimethyl-2,5-dihydro-1H-1lambda5-phosphol-1-one and its chiral derivatives, as well as expanded structure-activity relationship studies to optimize its pharmacological properties. The compound's unique electronic properties also suggest potential applications in photopharmacology.

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