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CS-W001157 4
Total: USD 88.00

3-(9-Carbazolyl)benzeneboronic acid

  • CAS No. 864377-33-3

  • Cat. No. CS-W003893
  • Purity≥98%
  • MDL No.MFCD18072506

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

3-(9-Carbazolyl)benzeneboronic acid|CS-W003893

Structure of 864377-33-3

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General Information

  • CAS No. 864377-33-3
  • Cat. No. CS-W003893
  • Purity ≥98%
  • MDL No. MFCD18072506
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₄BNO₂
  • Molecular Weight 287.12
  • Synonym(s) 3-(9H-Carbazol-9-yl)phenylboronic acid
  • SMILES OB(c1cccc(c1)n1c2ccccc2c2c1cccc2)O

Description

3-(9-Carbazolyl)benzeneboronic acid features a carbazolyl group conjugated to a boronic acid moiety, enabling efficient Suzuki-Miyaura coupling under mild conditions. The electron-rich carbazole enhances reactivity and stability, while the boronic acid facilitates C–C bond formation with aryl halides. This compound integrates seamlessly into advanced materials synthesis, particularly in organic electronics and fluorescent probe development.

Application

3-(9-Carbazolyl)benzeneboronic acid serves as a versatile building block for Suzuki-Miyaura coupling reactions, enabling the construction of biaryl scaffolds with applications in organic electronics and medicinal chemistry. The carbazolyl moiety provides enhanced π-conjugation and stability, while the boronic acid functionality offers reliable reactivity under mild conditions. Bench-stable and readily purified by recrystallization, it facilitates efficient synthesis of complex heterocyclic architectures and functionalized aryl systems in multistep sequences.

Synthesis

  • Route1

    References

    • EP1820801 A1, ; Page/Page column 84; 85 ;
  • Route2
    • In-stock
      9-(3-bromophenyl)carbazole|CS-0135829
      185112-61-2
    • null|null
      121-43-7
    • ~67%
    • In-stock
      3-(9-Carbazolyl)benzeneboronic acid|CS-W003893
      864377-33-3

    References

    • WO2013/12298 A1, ; Paragraph 103-104 ;
  • Route3
    • null|null
      86-74-8
    • ~%
    • In-stock
      3-(9-Carbazolyl)benzeneboronic acid|CS-W003893
      864377-33-3

    References

    • WO2013/12298 A1, ;

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   45.39
  • LogP   2.4635
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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