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CS-W001157 4
Total: USD 88.00

2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 190788-60-4

  • Cat. No. CS-W012915
  • Purity≥97%
  • MDL No.MFCD05863916

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

2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W012915

Structure of 190788-60-4

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General Information

  • CAS No. 190788-60-4
  • Cat. No. CS-W012915
  • Purity ≥97%
  • MDL No. MFCD05863916
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BO₃
  • Molecular Weight None
  • Synonym(s) 2-Methoxyphenylboronic Acid Pinacol Ester
  • SMILES COC1=C(C=CC=C1)B1OC(C)(C)C(C)(C)O1

Description

This boronate ester features a methoxy-substituted phenyl group coupled with a tetramethyl-1,3,2-dioxaborolane ring, delivering enhanced stability and solubility in organic media. The electron-rich aryl moiety facilitates efficient coupling in Suzuki-Miyaura reactions, while the sterically protected boron center ensures minimal hydrolysis under standard conditions. Ideal for late-stage functionalization and modular synthesis in medicinal chemistry workflows.

Application

2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its ortho-methoxy substitution enhances regioselectivity in heterocyclic coupling and improves solubility in common organic solvents. The tetramethyl-substituted dioxaborolane core ensures excellent stability and ease of purification, making it ideal for iterative synthesis of biaryl scaffolds and complex pharmaceutical intermediates.

Synthesis

  • Route1
    • In-stock
      1-Iodo-2-methoxybenzene|CS-W009305
      529-28-2
    • null|null
      25015-63-8
    • ~91%
    • In-stock
      2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W012915
      190788-60-4

    References

    • Journal of Organometallic Chemistry, , vol. 640, # 1-2 p. 197 - 199
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 135, # 50 p. 18730 - 18733
  • Route3
    • In-stock
      1-Bromo-2-methoxybenzene|CS-W007633
      578-57-4
    • null|null
      25015-63-8
    • ~87%
    • In-stock
      2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W012915
      190788-60-4

    References

    • Journal of Organic Chemistry, , vol. 73, # 14 p. 5589 - 5591

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P341-P312-P330-P363-P501

Quality Control

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Computational Chemistry Data

  • TPSA   27.69
  • LogP   1.9944
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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