Cas no 951307-27-0 (3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole)

3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole is a brominated derivative of indolo[3,2-b]carbazole, featuring octyl side chains at the 5 and 11 positions. This compound is of interest in organic electronics due to its extended π-conjugated system and enhanced solubility conferred by the dioctyl substituents. The dibromo functionalization facilitates further derivatization via cross-coupling reactions, making it a versatile intermediate for synthesizing optoelectronic materials. Its rigid, planar structure contributes to high charge carrier mobility, while the alkyl chains improve processability in solution-based fabrication. This compound is particularly relevant for applications in organic semiconductors, hole-transport materials, and light-emitting diodes (OLEDs). Its balanced electronic and morphological properties make it a promising candidate for advanced material research.
3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole structure
951307-27-0 structure
Product Name:3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole
CAS No:951307-27-0
MF:C34H42Br2N2
MW:638.518687725067
CID:1031077
PubChem ID:71607414
Update Time:2025-10-24

3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole Chemical and Physical Properties

Names and Identifiers

    • 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole
    • 3,9-dibromo-5,11-dioctylindolo[3,2-b]carbazole
    • CS-0435319
    • DTXSID60856363
    • 951307-27-0
    • Inchi: 1S/C34H42Br2N2/c1-3-5-7-9-11-13-19-37-31-21-25(35)15-17-27(31)29-24-34-30(23-33(29)37)28-18-16-26(36)22-32(28)38(34)20-14-12-10-8-6-4-2/h15-18,21-24H,3-14,19-20H2,1-2H3
    • InChI Key: HFMSSMCMAMHDMB-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2=C(C=1)N(CCCCCCCC)C1C=C3C4C=CC(=CC=4N(CCCCCCCC)C3=CC=12)Br

Computed Properties

  • Exact Mass: 638.16943g/mol
  • Monoisotopic Mass: 636.17147g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 38
  • Rotatable Bond Count: 14
  • Complexity: 644
  • 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: 12.8
  • Topological Polar Surface Area: 9.9?2

3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole Pricemore >>

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Additional information on 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole

Introduction to 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole (CAS No. 951307-27-0)

3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole, identified by its CAS number 951307-27-0, is a sophisticated organic compound belonging to the indolo[3,2-b]carbazole class. This heterocyclic structure has garnered significant attention in the field of pharmaceutical chemistry and materials science due to its unique molecular architecture and potential applications. The presence of bromine substituents and long-chain alkyl groups in its framework imparts distinct physicochemical properties, making it a subject of extensive research for various industrial and medicinal purposes.

The compound's structure consists of a fused indole and carbazole moiety, which is a privileged scaffold in drug discovery. The bromo atoms at the 3 and 9 positions enhance its reactivity, enabling further functionalization through cross-coupling reactions such as Suzuki or Buchwald-Hartwig couplings. These transformations are pivotal in synthesizing more complex derivatives with tailored biological activities. Additionally, the dioctyl side chains contribute to the compound's solubility and amphiphilic characteristics, which are crucial for formulating drug delivery systems and enhancing bioavailability.

Recent advancements in medicinal chemistry have highlighted the significance of indolo[3,2-b]carbazole derivatives in developing novel therapeutics. Studies have demonstrated that this class of compounds exhibits promising activities against various diseases, including cancer and infectious disorders. The brominated indolo[3,2-b]carbazole derivatives, such as 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole, have been investigated for their potential to inhibit kinases and other enzymes involved in pathogenic pathways. For instance, research has shown that modifications at the bromine positions can modulate the binding affinity and selectivity of these molecules towards target proteins.

In materials science, the unique electronic properties of 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole make it an attractive candidate for organic semiconductors and optoelectronic devices. The conjugated system formed by the indole and carbazole rings facilitates charge transport, which is essential for applications in organic light-emitting diodes (OLEDs), field-effect transistors (OFETs), and photovoltaic cells. The introduction of bulky alkyl groups improves film-forming properties and prevents aggregation-induced quenching of fluorescence, enhancing device performance.

The synthesis of 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole involves multi-step organic reactions starting from commercially available precursors. A common synthetic route includes bromination of an indolo[3,2-b]carbazole core followed by alkylation with 1-octene or its derivatives. The reaction conditions must be carefully optimized to ensure high yield and purity. Palladium-catalyzed cross-coupling reactions are often employed to introduce the bromine atoms efficiently. Post-synthetic modifications can further tailor the compound's properties for specific applications.

Biological evaluation of 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole has revealed intriguing pharmacological profiles. In vitro studies have shown that this compound exhibits inhibitory effects on certain kinases associated with cancer progression. The bromine substituents play a critical role in binding to these enzymes by forming hydrogen bonds or hydrophobic interactions with key residues in the active site. Additionally, the alkyl chains enhance membrane permeability, facilitating cellular uptake and improving intracellular distribution.

Preclinical studies are underway to assess the safety and efficacy of 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole in animal models. These investigations aim to determine optimal dosing regimens and evaluate potential side effects. The compound's structural features offer a promising foundation for developing next-generation therapeutics with improved pharmacokinetic profiles. Collaborative efforts between synthetic chemists and biologists are essential to translate laboratory findings into clinical applications.

The industrial relevance of 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole extends beyond pharmaceuticals into agrochemicals and specialty chemicals. Its derivatives can be functionalized to develop novel pesticides or crop protection agents. The compound's stability under various environmental conditions makes it suitable for formulation into environmentally friendly agrochemical products that maintain efficacy while minimizing ecological impact.

In conclusion,3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole (CAS No. 951307-27-0) is a versatile compound with diverse applications across multiple scientific disciplines。 Its unique structural features,including bromine substituents and octyl side chains,endow it with remarkable chemical reactivity and functional properties。 Ongoing research continues to uncover new possibilities for this molecule,underscoring its importance as a building block for innovative drug discovery,advanced materials,and sustainable industrial solutions。

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