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CS-W001157 4
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9-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

  • CAS No. 785051-54-9

  • Cat. No. CS-0097287
  • Purity≥97%
  • MDL No.MFCD16294549

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

9-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole|CS-0097287

Structure of 785051-54-9

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General Information

  • CAS No. 785051-54-9
  • Cat. No. CS-0097287
  • Purity ≥97%
  • MDL No. MFCD16294549
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₄H₂₄BNO₂
  • Molecular Weight 369.26
  • Synonym(s) 9-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(N3C4=C(C5=C3C=CC=C5)C=CC=C4)C=C2)O1

Description

This boronate-functionalized carbazole integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, offering robust stability under standard conditions. The tetramethyl-1,3,2-dioxaborolane moiety enables efficient C–C bond formation, while the electron-rich carbazole scaffold supports conjugated framework assembly in organic electronics and photoluminescent materials.

Application

9-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. The carbazole core provides structural rigidity and electron-rich character, while the pinacol boronate group enables efficient Suzuki-Miyaura coupling under mild conditions. Bench-stable and compatible with diverse functional groups, it facilitates the construction of biaryl scaffolds in pharmaceutical and materials chemistry.

Synthesis

  • Route1

    References

    • Chen, Bo; Ding, Junqiao; Wang, Lixiang; Jing, Xiabin; Wang, Fosong Chemical Communications, 2012 , vol. 48, # 71 p. 8970 - 8972
  • Route2
    • null|null
      61676-62-8
    • In-stock
      9-(4-Bromophenyl)-9H-carbazole|CS-W011997
      57102-42-8
    • ~83%
    • In-stock
      9-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole|CS-0097287
      785051-54-9

    References

    • Sun, Yi-Heng; Zhu, Xu-Hui; Chen, Zhao; Zhang, Yong; Cao, Yong Journal of Organic Chemistry, 2006 , vol. 71, # 16 p. 6281 - 6284
  • Route3
    • null|null
      1394130-73-4
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~51%
    • In-stock
      9-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole|CS-0097287
      785051-54-9

    References

    • Zhu, Chuan; Yamane, Motoki Organic Letters, 2012 , vol. 14, # 17 p. 4560 - 4563

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   23.39
  • LogP   5.0829
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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