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CS-W001157 4
Total: USD 88.00

(9-Phenyl-9H-carbazol-3-yl)boronic acid

  • CAS No. 854952-58-2

  • Cat. No. CS-W020553
  • Purity≥98%
  • MDL No.MFCD12196936

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

(9-Phenyl-9H-carbazol-3-yl)boronic acid|CS-W020553

Structure of 854952-58-2

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General Information

  • CAS No. 854952-58-2
  • Cat. No. CS-W020553
  • Purity ≥98%
  • MDL No. MFCD12196936
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₄BNO₂
  • Molecular Weight 287.12
  • Synonym(s) 9-Phenylcarbazol-3-yl boronic acid; N-phenylcarbazole-3-ylboronic acid
  • SMILES OB(C1=CC2=C(C=C1)N(C3=CC=CC=C3)C4=C2C=CC=C4)O

Description

This boronate moiety integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, delivering high yields under standard conditions. The carbazole scaffold imparts enhanced stability and solubility, while the phenyl group contributes to electron-rich character, enabling efficient coupling with aryl halides and triflates.

Application

(9-Phenyl-9H-carbazol-3-yl)boronic acid serves as a versatile building block in palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heterobiaryl architectures. Its stability under ambient conditions and compatibility with diverse functional groups facilitate straightforward purification and integration into complex molecular frameworks relevant to organic electronics and medicinal chemistry.

Synthesis

  • Route1

    References

    • WO2010/5066 A1, ; Page/Page column 197-198 ;
  • Route2
    • In-stock
      3-Bromo-9-phenyl-9H-carbazole|CS-W003820
      1153-85-1
    • null|null
      121-43-7
    • ~84%
    • In-stock
      (9-Phenyl-9H-carbazol-3-yl)boronic acid|CS-W020553
      854952-58-2

    References

    • EP1985613 A2, ; Page/Page column 62-63 ;
  • Route3
    • In-stock
      3-Bromo-9-phenyl-9H-carbazole|CS-W003820
      1153-85-1
    • null|null
      5419-55-6
    • ~70%
    • In-stock
      (9-Phenyl-9H-carbazol-3-yl)boronic acid|CS-W020553
      854952-58-2

    References

    • US2012/309974 A1, ; Page/Page column 13 ;

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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