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CS-W001157 4
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5-Fluoro-2-hydroxybenzeneboronic acid

  • CAS No. 259209-20-6

  • Cat. No. CS-W020608
  • Purity≥97%
  • MDL No.MFCD03095357

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

5-Fluoro-2-hydroxybenzeneboronic acid|CS-W020608

Structure of 259209-20-6

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General Information

  • CAS No. 259209-20-6
  • Cat. No. CS-W020608
  • Purity ≥97%
  • MDL No. MFCD03095357
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BFO₃
  • Molecular Weight 155.92
  • Synonym(s) 5-Fluoro-2-hydroxyphenylboronic acid
  • SMILES FC1=CC=C(O)C(B(O)O)=C1

Description

5-Fluoro-2-hydroxybenzeneboronic acid features a boronic acid group ortho to a phenolic hydroxyl, enabling efficient Suzuki-Miyaura coupling. The electron-withdrawing fluorine substituent enhances reactivity and stabilizes the boronate intermediate under physiological conditions. This bench-stable derivative integrates readily into complex molecular architectures with high functional group tolerance.

Application

5-Fluoro-2-hydroxybenzeneboronic 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 enhances boronate stability and facilitates chelation-assisted coupling, while the fluorine substituent provides orthogonal reactivity and metabolic stability in bioactive molecule synthesis. The compound exhibits excellent bench stability, simplifies purification, and functions reliably in complex molecular architectures.

Synthesis

  • Route1
    • null|null
      259209-11-5
    • ~47%
    • In-stock
      5-Fluoro-2-hydroxybenzeneboronic acid|CS-W020608
      259209-20-6

    References

    • Eukarion, Inc. Patent: US6177419 B1, 2001 ;
  • Route2
    • null|null
      10294-33-4
    • In-stock
      5-Fluoro-2-methoxyphenylboronic acid|CS-0007622
      179897-94-0
    • ~%
    • In-stock
      5-Fluoro-2-hydroxybenzeneboronic acid|CS-W020608
      259209-20-6

    References

    • US2003/114457 A1, ; US 20030114457 A1
  • Route3

    References

    • Angewandte Chemie - International Edition, , vol. 52, # 37 p. 9755 - 9758

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   60.69
  • LogP   -0.7889
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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