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CS-W001157 4
Total: USD 88.00

4-Biphenylboronic acid pinacol ester

  • CAS No. 144432-80-4

  • Cat. No. CS-W000872
  • Purity≥98%
  • MDL No.MFCD07368291

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

4-Biphenylboronic acid pinacol ester|CS-W000872

Structure of 144432-80-4

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General Information

  • CAS No. 144432-80-4
  • Cat. No. CS-W000872
  • Purity ≥98%
  • MDL No. MFCD07368291
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₁BO₂
  • Molecular Weight 280.17
  • Synonym(s) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl
  • SMILES CC(C(C)(O1)C)(OB1C2=CC=C(C3=CC=CC=C3)C=C2)C

Description

4-Biphenylboronic acid pinacol ester offers a stable, bench-stable boronate handle for Suzuki-Miyaura cross-coupling reactions. This derivative integrates seamlessly into complex molecular architectures, delivering reliable coupling efficiency under standard conditions. The pinacol protection enhances solubility and minimizes hydrolysis, enabling straightforward handling in synthetic workflows.

Application

4-Biphenylboronic acid pinacol ester serves as a stable, bench-friendly boronate building block for Suzuki-Miyaura cross-coupling reactions. Its pinacol ester protection enhances air and moisture stability, enabling reliable handling and purification. The molecule facilitates efficient C–C bond formation with aryl halides and pseudohalides under palladium catalysis, making it a practical reagent for constructing biaryl motifs in pharmaceutical and materials synthesis.

Synthesis

  • Route1
    • (2-(Dimethyl(phenyl)silyl)phenyl)methanol|CS-0579882
      853955-69-8
    • In-stock
      2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0036048
      68716-49-4
    • ~83%
    • In-stock
      4-Biphenylboronic acid pinacol ester|CS-W000872
      144432-80-4

    References

    • US2009/69577 A1, ; Page/Page column 24 ;
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 79, # 3 p. 888 - 900
  • Route3
    • In-stock
      4-Iodo-1,1'-biphenyl|CS-W002119
      1591-31-7
    • null|null
      25015-63-8
    • ~58%
    • In-stock
      4-Biphenylboronic acid pinacol ester|CS-W000872
      144432-80-4

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 3 p. 1397 - 1401

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

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.6528
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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