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CS-W001157 4
Total: USD 88.00

4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane

  • CAS No. 269410-26-6

  • Cat. No. CS-W000906
  • Purity≥97%
  • MDL No.MFCD06795691

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

4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane|CS-W000906

Structure of 269410-26-6

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General Information

  • CAS No. 269410-26-6
  • Cat. No. CS-W000906
  • Purity ≥97%
  • MDL No. MFCD06795691
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₁BO₃
  • Molecular Weight 296.17
  • Synonym(s) Phenoxyphenyl-4-boronic Acid Pinacol Ester
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(OC3=CC=CC=C3)C=C2)O1

Description

This boronate ester features a phenoxy-substituted aryl group paired with a tetramethylcyclohexadienone core, delivering enhanced stability and reactivity in Suzuki-Miyaura cross-coupling. The electron-rich aryl moiety facilitates efficient palladium-catalyzed bond formation under standard conditions.

Application

4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its tetramethyl substitution enhances oxidative stability and facilitates purification, while the phenoxy-substituted aryl group enables efficient coupling with diverse halides and pseudohalides. Functions reliably in standard reaction conditions to construct biaryl scaffolds common in pharmaceutical and materials chemistry.

Synthesis

  • Route1
    • In-stock
      1-Bromo-4-phenoxybenzene|CS-M1054
      101-55-3
    • null|null
      25015-63-8
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane|CS-W000906
      269410-26-6

    References

    • US6680401 B1, ; Page column 69 ;
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 24 p. 7543 - 7546
  • Route3

    References

    • Tetrahedron Letters, , vol. 54, # 2 p. 166 - 169

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

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Computational Chemistry Data

  • TPSA   27.69
  • LogP   3.7781
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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