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CS-W001157 4
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2-Hydroxyphenylboronic acid

  • CAS No. 89466-08-0

  • Cat. No. CS-W002733
  • Molecule weight137.93
  • Purity≥98%
  • MDL No.MFCD01074581

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

2-Hydroxyphenylboronic acid|CS-W002733

Structure of 89466-08-0

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General Information

  • CAS No. 89466-08-0
  • Cat. No. CS-W002733
  • Purity ≥98%
  • MDL No. MFCD01074581
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇BO₃
  • Molecular Weight 137.93
  • Synonym(s) None
  • SMILES OB(C1=CC=CC=C1O)O

Description

2-Hydroxyphenylboronic acid features a boronate moiety ortho to a phenolic hydroxyl group, enabling selective coordination in dynamic covalent chemistry. This arrangement enhances stability in aqueous environments and facilitates efficient coupling reactions under mild conditions. The compound serves as a key building block in the synthesis of functionalized aryl systems and bioconjugates.

Application

2-Hydroxyphenylboronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-hydroxyl group facilitates chelation-assisted coupling and enhances reaction selectivity. The compound exhibits good bench stability, ease of handling, and compatibility with diverse functional groups, making it well-suited for the synthesis of biaryl scaffolds and heterocyclic systems in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Tetrahedron Letters, , vol. 45, # 35 p. 6657 - 6660
  • Route2
    • null|null
      95-56-7
    • ~86%
    • In-stock
      2-Hydroxyphenylboronic acid|CS-W002733
      89466-08-0

    References

    • Tetrahedron Letters, , vol. 51, # 17 p. 2335 - 2338
  • Route3
    • null|null
      95-57-8
    • ~%
    • In-stock
      2-Hydroxyphenylboronic acid|CS-W002733
      89466-08-0

    References

    • Journal of the American Chemical Society, , vol. 134, # 28 p. 11667 - 11673

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H318
Precautionary Statements : P264-P270-P280-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   60.69
  • LogP   -0.928
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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