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CS-W001157 4
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3,6-Dibromo-9-ethyl-9H-carbazole

  • CAS No. 33255-13-9

  • Cat. No. CS-W009805
  • Purity≥98%
  • MDL No.MFCD00138134

*For research and further manufacturing use only, not for direct human use.

3,6-Dibromo-9-ethyl-9H-carbazole|CS-W009805

Structure of 33255-13-9

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General Information

  • CAS No. 33255-13-9
  • Cat. No. CS-W009805
  • Purity ≥98%
  • MDL No. MFCD00138134
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₁Br₂N
  • Molecular Weight 353.06
  • Synonym(s) 9H-carbazole, 3,6-dibromo-9-ethyl-
  • SMILES CCN1C2=C(C3=C1C=CC(Br)=C3)C=C(Br)C=C2

Description

3,6-Dibromo-9-ethyl-9H-carbazole features two bromine substituents at the 3 and 6 positions of the carbazole core, enhancing electrophilic reactivity for cross-coupling transformations. The ethyl group at the 9-position improves solubility and modulates electronic properties, enabling efficient incorporation into conjugated polymers and functional materials.

Application

3,6-Dibromo-9-ethyl-9H-carbazole serves as a versatile building block for the synthesis of functionalized carbazole derivatives. The dibromo substitution enables efficient Suzuki-Miyaura and Stille coupling reactions, facilitating the construction of conjugated polymers and bioactive heterocycles. The ethyl group at the 9-position enhances solubility and modulates electronic properties, while the bromine atoms offer high reactivity under standard palladium-catalyzed conditions. This compound exhibits excellent bench stability and is readily purified by column chromatography, making it well-suited for industrial R&D workflows in materials science and medicinal chemistry.

Synthesis

  • Route1

    References

    • Samsung Electronics Co., Ltd.; Yang, Hye-yeon; Joo, Won-jae; Son, Jhun-mo; Kang, Ho-suk Patent: US8558007 B2, 2013 ; Location in patent: Page/Page column 28; 29 ;
  • Route2
    • In-stock
      3,6-Dibromocarbazole|CS-W009870
      6825-20-3
    • null|null
      106-94-5
    • ~81%
    • In-stock
      3,6-Dibromo-9-ethyl-9H-carbazole|CS-W009805
      33255-13-9

    References

    • Shen, Ping; Tang, Yuhua; Jiang, Shenghui; Chen, Huajie; Zheng, Xiaoyan; Wang, Xueye; Zhao, Bin; Tan, Songting Organic Electronics: physics, materials, applications, 2011 , vol. 12, # 1 p. 125 - 135
  • Route3

    References

    • Recueil des Travaux Chimiques des Pays-Bas, , vol. 66, p. 533,541

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H318-H413
Precautionary Statements : P264-P270-P273-P280-P330-P501

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Computational Chemistry Data

  • TPSA   4.93
  • LogP   5.3394
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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