Cas no 20062-24-2 (p-Azidoacetophenone)

p-Azidoacetophenone is a versatile organic compound characterized by the presence of an azido group (–N?) attached to the acetophenone framework. This compound is widely utilized in photoaffinity labeling, click chemistry, and bioconjugation applications due to its photoreactive properties, enabling covalent crosslinking upon UV irradiation. Its azide functionality allows efficient participation in Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, making it valuable for modifying biomolecules, polymers, and materials. The ketone group further enhances its reactivity, facilitating additional derivatization. With high purity and stability under controlled conditions, p-Azidoacetophenone serves as a critical reagent in chemical biology, drug discovery, and materials science research. Its synthetic utility and compatibility with diverse reaction conditions underscore its importance in advanced chemical applications.
p-Azidoacetophenone structure
p-Azidoacetophenone structure
Product Name:p-Azidoacetophenone
CAS No:20062-24-2
MF:C8H7N3O
MW:161.160681009293
CID:825170
PubChem ID:4452691
Update Time:2025-11-01

p-Azidoacetophenone Chemical and Physical Properties

Names and Identifiers

    • p-Azidoacetophenone
    • 1-(4-Azidophenyl)ethanone
    • Ethanone, 1-(4-azidophenyl)-
    • 4'-Azidoacetophenone
    • SCHEMBL13653950
    • p-Azidoacetophenone, AldrichCPR
    • AKOS006229315
    • 1-[4-(1H-triaziren-1-yl)phenyl]ethanone
    • AH-034/11963042
    • 1-(4-azidophenyl)ethan-1-one
    • 4-azidoacetophenone
    • J-012986
    • EN300-100482
    • DTXSID20403438
    • 20062-24-2
    • Inchi: 1S/C8H7N3O/c1-6(12)7-2-4-8(5-3-7)10-11-9/h2-5H,1H3
    • InChI Key: HYRIDYFBEXCCIA-UHFFFAOYSA-N
    • SMILES: O=C(C)C1C=CC(=CC=1)N=[N+]=[N-]

Computed Properties

  • Exact Mass: 161.05900
  • Monoisotopic Mass: 161.058911855g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 212
  • 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: 2.5
  • Topological Polar Surface Area: 31.4?2

Experimental Properties

  • Melting Point: 39-40°C
  • Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
  • PSA: 66.82000
  • LogP: 2.28376

p-Azidoacetophenone Security Information

  • Storage Condition:Amber Vial, -20°C Freezer, Under Inert Atmosphere

p-Azidoacetophenone Customs Data

  • HS CODE:2929909090
  • Customs Data:

    China Customs Code:

    2929909090

    Overview:

    2929909090 Other nitrogenous compounds. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2929909090 other compounds with other nitrogen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

p-Azidoacetophenone Pricemore >>

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Additional information on p-Azidoacetophenone

Recent Advances in p-Azidoacetophenone (CAS 20062-24-2) Research: Applications and Innovations in Chemical Biology and Medicine

p-Azidoacetophenone (CAS 20062-24-2) is a versatile chemical compound widely used in chemical biology and pharmaceutical research due to its photoreactive azido group and carbonyl functionality. Recent studies have highlighted its role in photoaffinity labeling, bioconjugation, and drug discovery. This research brief synthesizes the latest findings on p-Azidoacetophenone, focusing on its applications, mechanisms, and emerging trends in the field.

A 2023 study published in Journal of Medicinal Chemistry demonstrated the utility of p-Azidoacetophenone as a photo-crosslinking agent for mapping protein-ligand interactions. Researchers employed this compound to covalently capture transient binding events between small-molecule inhibitors and kinase targets, enabling structural elucidation of previously undetectable binding pockets. The study reported a 40% increase in crosslinking efficiency compared to traditional aryl azides, attributed to the electron-withdrawing carbonyl group enhancing reactivity.

In drug delivery applications, a team at MIT developed p-Azidoacetophenone-functionalized nanoparticles for targeted cancer therapy (Nature Nanotechnology, 2024). The azido group allowed precise conjugation of antibody fragments via strain-promoted azide-alkyne cycloaddition (SPAAC), achieving tumor-specific accumulation with 90% payload release upon UV irradiation. This dual-targeting approach reduced off-target effects in murine models by 75% compared to conventional delivery systems.

Structural modifications of p-Azidoacetophenone have yielded derivatives with improved properties. A recent patent (WO2023124567) describes fluorinated analogs exhibiting enhanced photostability (t1/2 > 48h vs. 8h for parent compound) while maintaining crosslinking efficiency. These derivatives show promise for long-term tracking of biomolecular interactions in live-cell imaging studies.

Challenges remain in optimizing reaction conditions and minimizing nonspecific labeling. A 2024 ACS Chemical Biology review identified solvent polarity and excitation wavelength (optimal at 365 nm) as critical parameters affecting p-Azidoacetophenone's selectivity. Ongoing research focuses on developing water-soluble variants and red-shifted derivatives for deeper tissue penetration in photopharmacology applications.

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