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CS-W001157 4
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4,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane

  • CAS No. 287944-05-2

  • Cat. No. CS-0030002
  • Molecule weight284.20
  • Purity≥95%
  • MDL No.MFCD11520534

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

4,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane|CS-0030002

Structure of 287944-05-2

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General Information

  • CAS No. 287944-05-2
  • Cat. No. CS-0030002
  • Purity ≥95%
  • MDL No. MFCD11520534
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₅BO₂
  • Molecular Weight 284.20
  • Synonym(s) 4-Phenyl-1-cyclohexen-1-ylboronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CCC(C3=CC=CC=C3)CC2)O1

Description

This boronate ester features a tetrahydrobiphenyl moiety that enhances stability and solubility in organic media. The tetramethyl substitution pattern minimizes protodeboronation, enabling reliable cross-coupling under standard conditions. This robust scaffold integrates seamlessly into Suzuki-Miyaura reactions, delivering high yields with minimal side products.

Application

4,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its tetramethyl-substituted dioxaborolane ring enhances hydrolytic stability and functional group tolerance, while the 1,2,3,6-tetrahydronaphthalene moiety provides a rigid, electron-rich aryl handle ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      122948-47-4
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~81%
    • In-stock
      4,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane|CS-0030002
      287944-05-2

    References

    • Hunt, Hazel J.; Ray, Nicholas C.; Hynd, George; Sutton, Jon; Sajad, Mohammed; O'Connor, Elizabeth; Ahmed, Shahadat; Lockey, Peter; Daly, Steve; Buckley, Gerry; Clark, Robin D.; Roe, Robert; Blasey, Christine; Belanoff, Joe Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 24 p. 7376 - 7380
  • Route2
    • null|null
      61676-62-8
    • null|null
      86724-17-6
    • ~70%
    • In-stock
      4,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane|CS-0030002
      287944-05-2

    References

    • Rauniyar, Vivek; Zhai, Huimin; Hall, Dennis G. Journal of the American Chemical Society, 2008 , vol. 130, # 26 p. 8481 - 8490
  • Route3

    References

    • CORCEPT THERAPEUTICS, INC.; CLARK, Robin; HYND, George; RAY, Nicholas; SAJAD, Mohammad Patent: WO2012/129074 A1, 2012 ; WO 2012/129074 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

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   4.5119
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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