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CS-W001157 4
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(5-Chloro-2-hydroxyphenyl)boronic acid

  • CAS No. 89488-25-5

  • Cat. No. CS-0008642
  • Purity≥97%
  • MDL No.MFCD06659863

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

(5-Chloro-2-hydroxyphenyl)boronic acid|CS-0008642

Structure of 89488-25-5

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General Information

  • CAS No. 89488-25-5
  • Cat. No. CS-0008642
  • Purity ≥97%
  • MDL No. MFCD06659863
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BClO₃
  • Molecular Weight 172.37
  • Synonym(s) Boronic acid, B-(5-chloro-2-hydroxyphenyl)-
  • SMILES OB(C1=CC(Cl)=CC=C1O)O

Description

This boronic acid features a chlorinated hydroxyphenyl scaffold, enabling direct incorporation into Suzuki-Miyaura couplings. The ortho-hydroxyl group enhances reactivity and facilitates chelation during transition metal-catalyzed transformations. Bench-stable under standard conditions, it offers reliable performance in synthetic sequences requiring precise functional group tolerance.

Application

(5-Chloro-2-hydroxyphenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. The ortho-hydroxyl group provides enhanced stability and facilitates directed metalation, while the chloro substituent offers compatibility with cross-coupling protocols. Its bench-stable nature and straightforward purification make it ideal for constructing complex phenolic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Angewandte Chemie - International Edition, , vol. 52, # 37 p. 9755 - 9758
  • Route2

    References

    • Tetrahedron, , vol. 19, p. 821 - 826

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H318
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   60.69
  • LogP   -0.2746
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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