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CS-W001157 4
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9-Phenanthreneboronic acid

  • CAS No. 68572-87-2

  • Cat. No. CS-W002428
  • Purity≥98%
  • MDL No.MFCD00143524
  • AREC Toxic Substance

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

9-Phenanthreneboronic acid|CS-W002428

Structure of 68572-87-2

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General Information

  • CAS No. 68572-87-2
  • Cat. No. CS-W002428
  • Purity ≥98%
  • MDL No. MFCD00143524
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₁BO₂
  • Molecular Weight 222.05
  • Synonym(s) Phenanthreneboronicacid; 9-Phenanthreneboronic acid
  • SMILES OB(c1cc2ccccc2c2c1cccc2)O

Description

9-Phenanthreneboronic acid integrates a rigid, electron-rich phenanthrene scaffold with a boronic acid handle, enabling efficient Suzuki-Miyaura coupling under standard conditions. This bench-stable reagent facilitates the construction of complex polycyclic architectures in synthetic organic chemistry and materials science applications.

Application

9-Phenanthreneboronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. Its phenanthrene scaffold provides structural rigidity and enhanced stability compared to simpler aryl boronic acids, while the boronic acid group exhibits good bench stability and compatibility with diverse functional groups. Facilitates access to extended π-conjugated systems relevant to organic semiconductors and fluorescent materials.

Synthesis

  • Route1
    • null|null
      5419-55-6
    • In-stock
      9-Bromophenanthrene|CS-W012551
      573-17-1
    • ~91%
    • In-stock
      9-Phenanthreneboronic acid|CS-W002428
      68572-87-2

    References

    • WO2006/135973 A1, ; Page/Page column 31 ;
  • Route2

    References

    • New Journal of Chemistry, , vol. 32, # 11 p. 1847 - 1849
  • Route3

    References

    • Naturwissenschaften, , vol. 45, p. 543

Safety Information

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

Quality Control

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Computational Chemistry Data

  • TPSA   40.46
  • LogP   1.6728
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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