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CS-W001157 4
Total: USD 88.00

[1,1'-Biphenyl]-4-ylboronic acid

  • CAS No. 5122-94-1

  • Cat. No. CS-W002364
  • Purity≥98%
  • MDL No.MFCD00093311

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

[1,1'-Biphenyl]-4-ylboronic acid|CS-W002364

Structure of 5122-94-1

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General Information

  • CAS No. 5122-94-1
  • Cat. No. CS-W002364
  • Purity ≥98%
  • MDL No. MFCD00093311
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₁BO₂
  • Molecular Weight 198.03
  • Synonym(s) None
  • SMILES OB(c1ccc(cc1)c1ccccc1)O

Description

1,1'-Biphenyl]-4-ylboronic acid features a sterically hindered biphenyl scaffold that enhances stability and facilitates efficient cross-coupling reactions. This bench-stable boronic acid integrates readily into Suzuki-Miyaura protocols, enabling reliable C–C bond formation under mild conditions. The electron-deficient aryl moiety promotes high reactivity in transition-metal-catalyzed transformations.

Application

[1,1'-Biphenyl]-4-ylboronic acid serves as a versatile building block in palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. Its biphenyl scaffold offers enhanced stability and orthogonal reactivity, facilitating the synthesis of biaryl motifs common in pharmaceuticals and functional materials. The boronic acid group exhibits excellent bench stability, tolerates diverse functional groups, and enables straightforward purification, making it well-suited for iterative synthesis and scale-up applications.

Synthesis

  • Route1

    References

    • ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; EUM, Sung Jin; KWON, Hyuck Joo; KIM, Bong Ok; KIM, Sung Min; YOON, Seung Soo Patent: WO2011/105700 A1, 2011 ; Location in patent: Page/Page column 18; 19; 21; 22 ;
  • Route2
    • null|null
      121-43-7
    • In-stock
      4-Bromobiphenyl|CS-D1553
      92-66-0
    • ~86%
    • In-stock
      [1,1'-Biphenyl]-4-ylboronic acid|CS-W002364
      5122-94-1

    References

    • Dingemans, Theo J.; Murthy, N. Sanjeeva; Samulski, Edward T. Journal of Physical Chemistry B, 2001 , vol. 105, # 37 p. 8845 - 8860
  • Route3
    • null|null
      5419-55-6
    • In-stock
      4-Bromobiphenyl|CS-D1553
      92-66-0
    • ~90%
    • In-stock
      [1,1'-Biphenyl]-4-ylboronic acid|CS-W002364
      5122-94-1

    References

    • Agouron Pharmaceuticals, Inc.; Syntex (U.S.A.), Inc. Patent: US6008243 A1, 1999 ;

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   40.46
  • LogP   1.0334
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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