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CS-W001157 4
Total: USD 88.00

(3-(Adamantan-1-yl)-4-methoxyphenyl)boronic acid

  • CAS No. 459423-32-6

  • Cat. No. CS-0150599
  • Purity≥97%
  • MDL No.MFCD08056355

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

(3-(Adamantan-1-yl)-4-methoxyphenyl)boronic acid|CS-0150599

Structure of 459423-32-6

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General Information

  • CAS No. 459423-32-6
  • Cat. No. CS-0150599
  • Purity ≥97%
  • MDL No. MFCD08056355
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₃BO₃
  • Molecular Weight 286.17
  • Synonym(s) 3-(1-Adamantyl)-4-methoxyphenylboronic acid
  • SMILES COC1=C(C=C(C=C1)B(O)O)C23CC4CC(CC(C4)C2)C3

Description

This boronate moiety integrates a bulky adamantan-1-yl group with a methoxy-substituted phenyl ring, delivering enhanced stability and solubility in polar solvents. The electron-rich aryl system enables efficient coupling in Suzuki-Miyaura reactions under standard conditions.

Application

(3-(Adamantan-1-yl)-4-methoxyphenyl)boronic acid serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. Its adamantan-1-yl moiety imparts enhanced steric bulk and metabolic stability, while the methoxy group provides predictable electronic modulation. The boronic acid functionality enables efficient coupling with aryl halides and triflates under mild conditions, facilitating access to complex biaryl architectures relevant in medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      5419-55-6
    • ~95%
    • In-stock
      (3-(Adamantan-1-yl)-4-methoxyphenyl)boronic acid|CS-0150599
      459423-32-6

    References

    • WO2006/108717 A2, ; Page/Page column 8-9 ;
  • Route2

    References

    • WO2005/108338 A1, ; Page/Page column 48 ; WO 2005/108338 A1
  • Route3

    References

    • US2010/113816 A1, ; Page/Page column 3 ;

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   49.69
  • LogP   1.8428
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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