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CS-W001157 4
Total: USD 88.00

2-Methoxyphenylboronic acid

  • CAS No. 5720-06-9

  • Cat. No. CS-W002569
  • Purity≥98%
  • MDL No.MFCD00236047

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

2-Methoxyphenylboronic acid|CS-W002569

Structure of 5720-06-9

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General Information

  • CAS No. 5720-06-9
  • Cat. No. CS-W002569
  • Purity ≥98%
  • MDL No. MFCD00236047
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉BO₃
  • Molecular Weight None
  • Synonym(s) None
  • SMILES COC1=CC=CC=C1B(O)O

Description

2-Methoxyphenylboronic acid features a boronate moiety attached to a methoxy-substituted aromatic ring, delivering enhanced solubility and stability in aqueous-organic mixtures. This bench-stable reagent facilitates efficient Suzuki-Miyaura coupling under mild conditions, enabling rapid construction of biaryl architectures in medicinal chemistry and materials synthesis.

Application

2-Methoxyphenylboronic acid serves as a reliable building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-methoxy substituent enhances stability and solubility while maintaining compatibility with diverse functional groups. The compound exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for iterative synthesis of biaryl scaffolds and complex heterocycles in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Fukuda, Tsutomu; Sudo, Ei-ichi; Shimokawa, Kozue; Iwao, Masatomo Tetrahedron, 2008 , vol. 64, # 2 p. 328 - 338
  • Route2

    References

    • Pennington, Thomas E.; Kardiman, Cynantya; Hutton, Craig A. Tetrahedron Letters, 2004 , vol. 45, # 35 p. 6657 - 6660
  • Route3
    • null|null
      5419-55-6
    • In-stock
      1-Bromo-2-methoxybenzene|CS-W007633
      578-57-4
    • ~71%
    • In-stock
      2-Methoxyphenylboronic acid|CS-W002569
      5720-06-9

    References

    • Lloyd, David G.; Hughes, Rosario B.; Zisterer, Daniela M.; Williams, D. Clive; Fattorusso, Caterina; Catalanotti, Bruno; Campiani, Giuseppe; Meegan, Mary J. Journal of Medicinal Chemistry, 2004 , vol. 47, # 23 p. 5612 - 5615

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : 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   49.69
  • LogP   -0.625
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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