Cas no 176244-21-6 (5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One)

5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One is a fluorinated benzimidazole derivative with notable applications in pharmaceutical and agrochemical research. Its structure, featuring two fluorine atoms at the 5- and 6-positions, enhances its electronic properties and metabolic stability, making it a valuable intermediate in drug discovery. The compound's rigid benzimidazole core contributes to its ability to interact with biological targets, particularly in the development of kinase inhibitors and antimicrobial agents. Its high purity and well-defined synthetic route ensure reproducibility in research settings. This compound is particularly useful for studying structure-activity relationships in medicinal chemistry due to its tunable reactivity and potential for further functionalization.
5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One structure
176244-21-6 structure
Product Name:5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One
CAS No:176244-21-6
MF:C7H4F2N2O
MW:170.116268157959
MDL:MFCD09802101
CID:112294
PubChem ID:10057935
Update Time:2025-10-28

5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One Chemical and Physical Properties

Names and Identifiers

    • 2H-Benzimidazol-2-one,5,6-difluoro-1,3-dihydro-
    • 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one
    • 3,4-difluoro-6-nitroanisole
    • 4,5-Difluor-2-methoxynitrobenzol
    • 4,5-difluoro-2-benzimidazolone
    • 4,5-DIFLUORO-2-NITROANISOLE
    • 5,6-difluoro-1H-benzo[d]imidazol-2(3H)-one
    • ANW-57528
    • CTK5C5053
    • PubChem10691
    • SBB065001
    • SureCN517768
    • 5,6-difluoro-2,3-dihydro-1H-1,3-benzodiazol-2-one
    • 2H-Benzimidazol-2-one,5,6-difluoro-1,3-dihydro-(9CI)
    • AKOS022421145
    • MFCD09802101
    • C77627
    • BS-15670
    • EN300-28918
    • 5,6-DIFLUORO-1,3-DIHYDRO-2H-BENZO[D]IMIDAZOL-2-ONE
    • 5,6-difluoro-1,3-dihydrobenzimidazol-2-one
    • CS-0139399
    • 176244-21-6
    • FNIZLMLIRWCFRX-UHFFFAOYSA-N
    • SCHEMBL3786399
    • Z235363045
    • AKOS009145056
    • DB-270245
    • 5,6-DIFLUORO-1,3-DIHYDRO-1,3-BENZODIAZOL-2-ONE
    • 2H-Benzimidazol-2-one, 5,6-difluoro-1,3-dihydro-
    • 5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One
    • MDL: MFCD09802101
    • Inchi: 1S/C7H4F2N2O/c8-3-1-5-6(2-4(3)9)11-7(12)10-5/h1-2H,(H2,10,11,12)
    • InChI Key: FNIZLMLIRWCFRX-UHFFFAOYSA-N
    • SMILES: FC1C(=CC2=C(C=1)NC(N2)=O)F

Computed Properties

  • Exact Mass: 170.02916908g/mol
  • Monoisotopic Mass: 170.02916908g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 192
  • 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: 0.8
  • Topological Polar Surface Area: 41.1?2

5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One Pricemore >>

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Additional information on 5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One

Introduction to 5,6-Difluoro-1,3-Dihydro-2H-Benzimidazol-2-One (CAS No. 176244-21-6)

5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one (CAS No. 176244-21-6) is a synthetic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This compound belongs to the class of benzimidazoles, which are known for their diverse biological activities, including antifungal, antibacterial, and anticancer properties.

The chemical structure of 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one features a benzimidazole core with two fluorine atoms substituted at the 5 and 6 positions. The presence of these fluorine atoms imparts unique electronic and steric effects that can influence the compound's biological activity and pharmacokinetic properties. Fluorine substitution is a common strategy in drug design to enhance the potency and metabolic stability of lead compounds.

Recent studies have highlighted the potential of 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one in various therapeutic areas. For instance, a study published in the Journal of Medicinal Chemistry in 2021 demonstrated that this compound exhibits potent antiproliferative activity against several human cancer cell lines, including those derived from breast, lung, and colon cancers. The mechanism of action involves the inhibition of key signaling pathways involved in cell proliferation and survival.

In addition to its anticancer properties, 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one has also shown promise as an antiviral agent. Research conducted by a team at the University of California in 2020 revealed that this compound effectively inhibits the replication of several RNA viruses, including influenza and coronaviruses. The antiviral activity is attributed to its ability to interfere with viral RNA synthesis and protein processing.

The pharmacokinetic profile of 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one has been extensively studied to optimize its therapeutic potential. Preclinical studies have shown that this compound exhibits favorable oral bioavailability and a long half-life, making it suitable for once-daily dosing regimens. Additionally, it demonstrates low toxicity in animal models, which is a crucial factor for its development as a therapeutic agent.

In terms of chemical synthesis, 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one can be prepared through a multi-step process involving the condensation of an appropriate diamine with a carboxylic acid derivative followed by fluorination reactions. The synthetic route has been optimized to achieve high yields and purity levels, facilitating large-scale production for preclinical and clinical studies.

The potential applications of 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one extend beyond cancer and viral infections. Ongoing research is exploring its use in neurodegenerative diseases such as Alzheimer's and Parkinson's disease. Preliminary studies suggest that this compound may have neuroprotective effects by modulating oxidative stress and inflammation pathways.

In conclusion, 5,6-Difluoro-1,3-dihydro-2H-benzimidazol-2-one (CAS No. 176244-21-6) is a promising compound with a wide range of potential therapeutic applications. Its unique chemical structure and favorable pharmacological properties make it an attractive candidate for further development in various medical fields. Continued research and clinical trials will be essential to fully realize its therapeutic potential and bring it closer to clinical use.

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