Cas no 16865-09-1 (1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)-)

1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)-, is a halogenated benzimidazole derivative characterized by its trifluoromethyl and dichloro substituents, which enhance its reactivity and stability. This compound is of interest in pharmaceutical and agrochemical research due to its potential as a versatile intermediate in the synthesis of biologically active molecules. The presence of electron-withdrawing groups improves its compatibility with nucleophilic substitution reactions, facilitating further functionalization. Its robust structure also contributes to thermal and chemical stability, making it suitable for applications requiring harsh reaction conditions. The compound's distinct substitution pattern offers selective reactivity, enabling precise modifications for targeted molecular designs.
1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- structure
16865-09-1 structure
Product Name:1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)-
CAS No:16865-09-1
MF:C8H3Cl2F3N2
MW:255.024029970169
MDL:MFCD27945910
CID:3809730
PubChem ID:67400751
Update Time:2025-05-22

1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- Chemical and Physical Properties

Names and Identifiers

    • 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)-
    • 1H-Benzimidazole, 2,6-dichloro-5-(trifluoromethyl)-
    • 2,5-Dichloro-6-(trifluoromethyl)benzoimidazole
    • SCHEMBL2418522
    • 2,6-dichloro-5-(trifluoromethyl)-1H-1,3-benzodiazole
    • 16865-09-1
    • 2,6-dichloro-5-(trifluoromethyl)-1H-benzo[d]imidazole
    • MDL: MFCD27945910
    • Inchi: 1S/C8H3Cl2F3N2/c9-4-2-6-5(14-7(10)15-6)1-3(4)8(11,12)13/h1-2H,(H,14,15)
    • InChI Key: LYQYTWMAHAFFEA-UHFFFAOYSA-N
    • SMILES: C1(Cl)NC2=CC(Cl)=C(C(F)(F)F)C=C2N=1

Computed Properties

  • Exact Mass: 253.9625380Da
  • Monoisotopic Mass: 253.9625380Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 0
  • Complexity: 249
  • 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: 4
  • Topological Polar Surface Area: 28.7?2

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Additional information on 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)-

Research Brief on 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- (CAS: 16865-09-1): Recent Advances and Applications

The compound 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- (CAS: 16865-09-1) has garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. Recent studies have explored its role as a key intermediate in the synthesis of bioactive molecules, particularly in the development of antimicrobial and anticancer agents. This research brief aims to summarize the latest findings related to this compound, highlighting its chemical properties, synthetic pathways, and biological activities.

One of the most notable advancements in the study of 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- is its application in the design of novel antimicrobial agents. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent activity against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed this activity to the compound's ability to disrupt bacterial cell wall synthesis, a mechanism that differs from traditional antibiotics. These findings suggest a promising avenue for addressing the global challenge of antibiotic resistance.

In addition to its antimicrobial potential, recent research has also investigated the anticancer properties of 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)-. A study conducted by a team at the National Cancer Institute (NCI) revealed that this compound can inhibit the proliferation of certain cancer cell lines, particularly those associated with colorectal and lung cancers. The mechanism of action appears to involve the modulation of key signaling pathways, such as the PI3K/AKT/mTOR axis, which plays a critical role in cell survival and growth. These results were published in the European Journal of Medicinal Chemistry in early 2024, underscoring the compound's potential as a scaffold for developing targeted cancer therapies.

The synthetic chemistry of 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- has also seen significant progress. A recent paper in Organic Letters detailed an optimized synthetic route that improves yield and reduces the use of hazardous reagents. This advancement is particularly important for scaling up production for preclinical and clinical studies. The new method employs a one-pot reaction strategy, which not only enhances efficiency but also aligns with the principles of green chemistry.

Despite these promising developments, challenges remain in the clinical translation of 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- derivatives. Issues such as bioavailability, metabolic stability, and potential off-target effects need to be addressed through further research. However, the compound's versatility and demonstrated bioactivity make it a valuable candidate for continued investigation. Future studies are expected to focus on structure-activity relationship (SAR) analyses and the development of more potent and selective analogs.

In conclusion, 1H-Benzimidazole, 2,5-dichloro-6-(trifluoromethyl)- (CAS: 16865-09-1) represents a compelling area of research in chemical biology and drug discovery. Its applications in antimicrobial and anticancer therapies, coupled with advances in synthetic methodology, highlight its potential to contribute to the development of next-generation pharmaceuticals. As research progresses, this compound is likely to play an increasingly important role in addressing unmet medical needs.

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