Cas no 3652-89-9 (4-Bromo-9H-carbazole)

4-Bromo-9H-carbazole is a brominated derivative of carbazole, a heterocyclic aromatic compound widely utilized in organic synthesis and materials science. This compound serves as a versatile intermediate in the preparation of pharmaceuticals, agrochemicals, and optoelectronic materials, particularly in the development of organic light-emitting diodes (OLEDs) and charge-transporting polymers. The bromine substituent enhances its reactivity, enabling efficient cross-coupling reactions such as Suzuki or Buchwald-Hartwig amination. Its high purity and stability make it suitable for precision applications in research and industrial processes. The rigid carbazole core contributes to desirable electronic properties, facilitating its use in advanced functional materials.
4-Bromo-9H-carbazole structure
4-Bromo-9H-carbazole structure
Product Name:4-Bromo-9H-carbazole
CAS No:3652-89-9
MF:C12H8BrN
MW:246.102622032166
MDL:MFCD18450175
CID:1476152
PubChem ID:253660817
Update Time:2025-06-09

4-Bromo-9H-carbazole Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-9H-carbazole
    • 9H-Carbazole, 4-bromo-
    • 4-Bromocarbazole
    • 4-Brom-butyroylbromid
    • 4-Brom-butyrylbromid
    • 4-Brom-carbazol
    • 4-bromo-butyryl bromide
    • 4-bromo-carbazole
    • Butanoyl bromide,4-bromo
    • SB66907
    • 3652-89-9
    • MFCD18450175
    • DA-19657
    • 4-Bromocarbazole; 9H-Carbazole, 4-bromo-;Carbazole, 4-bromo-
    • CS-0028332
    • AKOS027250600
    • 4-Bromo carbazole;9H-carbazole,4-bromo
    • BCP32102
    • B4752
    • CHEMBL5084185
    • A852691
    • F16196
    • SY031155
    • AS-10418
    • AC-33531
    • AMY19499
    • 5-bromocarbazole
    • SCHEMBL420335
    • MDL: MFCD18450175
    • Inchi: 1S/C12H8BrN/c13-9-5-3-7-11-12(9)8-4-1-2-6-10(8)14-11/h1-7,14H
    • InChI Key: CBJHFGQCHKNNJY-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC2=C1C1C=CC=CC=1N2

Computed Properties

  • Exact Mass: 244.98400
  • Monoisotopic Mass: 244.98401g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 0
  • Complexity: 218
  • 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: 4.6
  • Topological Polar Surface Area: 15.8?2

Experimental Properties

  • Density: 1.617±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 105.0 to 109.0 deg-C
  • Boiling Point: 409.2°C at 760 mmHg
  • Solubility: Insuluble (2.3E-3 g/L) (25 oC),
  • PSA: 15.79000
  • LogP: 4.08360

4-Bromo-9H-carbazole Security Information

4-Bromo-9H-carbazole Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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4-Bromo-9H-carbazole Suppliers

Amadis Chemical Company Limited
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(CAS:3652-89-9)4-Bromo-9H-carbazole
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Purity:99%
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Shaanxi pure crystal photoelectric technology co. LTD
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(CAS:3652-89-9)4-Bromo-9H-carbazole
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Suzhou Senfeida Chemical Co., Ltd
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(CAS:3652-89-9)4-BroMo-9H-carbazole
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(CAS:3652-89-9)4-溴咔唑
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Additional information on 4-Bromo-9H-carbazole

Introduction to 4-Bromo-9H-carbazole (CAS No. 3652-89-9)

4-Bromo-9H-carbazole, identified by its Chemical Abstracts Service (CAS) number 3652-89-9, is a significant heterocyclic organic compound that has garnered considerable attention in the field of pharmaceutical chemistry and materials science. This compound belongs to the carbazole family, a class of nitrogen-containing aromatic organic compounds known for their diverse biological activities and structural versatility. The presence of a bromine substituent at the 4-position enhances its utility as a key intermediate in synthetic chemistry, particularly in the development of novel therapeutic agents and advanced materials.

The structural framework of 4-Bromo-9H-carbazole consists of a fused benzene and pyridine ring system, with the bromine atom attached to one of the aromatic carbon atoms. This configuration imparts unique electronic and steric properties, making it a valuable building block for constructing more complex molecular architectures. In recent years, the demand for this compound has surged due to its role in synthesizing bioactive molecules, including kinase inhibitors, antimicrobial agents, and photoactive materials.

One of the most compelling aspects of 4-Bromo-9H-carbazole is its applications in medicinal chemistry. Researchers have leveraged its scaffold to develop inhibitors targeting various disease-related proteins. For instance, studies have demonstrated its utility in creating small-molecule modulators of protein-protein interactions, which are crucial for understanding cellular signaling pathways. The bromine substituent facilitates further functionalization through cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings, enabling the introduction of diverse pharmacophores.

Recent advancements in drug discovery have highlighted the importance of 4-Bromo-9H-carbazole in designing next-generation therapeutics. Its incorporation into drug candidates has shown promise in preclinical studies for treating conditions such as cancer, inflammation, and neurodegenerative disorders. The compound’s ability to act as a precursor for derivatives with enhanced binding affinity and selectivity has made it a cornerstone in structure-activity relationship (SAR) studies.

In materials science, 4-Bromo-9H-carbazole has found applications in the development of organic semiconductors and light-emitting diodes (OLEDs). Its conjugated system and halogen substitution contribute to tunable electronic properties, making it suitable for optoelectronic devices. Researchers have explored its use in fabricating organic field-effect transistors (OFETs) and photovoltaic cells, where its molecular structure allows for efficient charge transport and luminescence.

The synthesis of 4-Bromo-9H-carbazole typically involves bromination of carbazole precursors using brominating agents such as N-bromosuccinimide (NBS). This method is favored for its high regioselectivity and moderate reaction conditions. Alternative synthetic routes include palladium-catalyzed cross-coupling reactions starting from halogenated carbazole derivatives, which offer greater flexibility in introducing additional functional groups.

The chemical reactivity of 4-Bromo-9H-carbazole extends beyond pharmaceutical applications. It serves as a versatile intermediate in polymer chemistry, where it is incorporated into conjugated polymers for use in flexible electronics. The bromine atom allows for post-polymerization modifications, enabling the tuning of polymer properties such as solubility and thermal stability.

Industrial-scale production of 4-Bromo-9H-carbazole requires careful optimization to ensure high yield and purity. Process chemists focus on minimizing side reactions and improving atom economy to enhance sustainability. Advances in green chemistry have led to the adoption of solvent-free conditions and catalytic methods, reducing environmental impact while maintaining efficiency.

The future prospects of 4-Bromo-9H-carbazole are promising, with ongoing research exploring new synthetic methodologies and applications. Innovations in computational chemistry are aiding in the design of novel derivatives with tailored properties using machine learning algorithms. Additionally, collaborations between academia and industry are driving the development of innovative formulations for drug delivery systems incorporating this compound.

In conclusion, 4-Bromo-9H-carbazole (CAS No. 3652-89-9) is a multifaceted compound with far-reaching implications in pharmaceuticals and materials science. Its unique structural features and reactivity make it indispensable in modern chemical research. As scientific understanding evolves, so too will the applications and significance of this remarkable molecule.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:3652-89-9)4-Bromo-9H-carbazole
A852691
Purity:99%
Quantity:100g
Price ($):374.0
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Shaanxi pure crystal photoelectric technology co. LTD
(CAS:3652-89-9)4-Bromo-9H-carbazole
CJC002
Purity:99%
Quantity:1kg
Price ($):Inquiry
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