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CS-W001157 4
Total: USD 88.00

4-Borono-2-nitrobenzoic acid

  • CAS No. 80500-28-3

  • Cat. No. CS-0036949
  • Purity≥98%
  • MDL No.None

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

4-Borono-2-nitrobenzoic acid|CS-0036949

Structure of 80500-28-3

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General Information

  • CAS No. 80500-28-3
  • Cat. No. CS-0036949
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BNO₆
  • Molecular Weight 210.94
  • Synonym(s) 4-Carboxy-3-nitrobenzeneboronic Acid (contains varying amounts of Anhydride)
  • SMILES C1=C(C=C(C(=C1)C(=O)O)[N+](=O)[O-])B(O)O

Description

4-Borono-2-nitrobenzoic acid features a boronate moiety paired with a nitro group and carboxylic acid functionality, enabling selective conjugation in bioorthogonal reactions. The electron-deficient aromatic core enhances reactivity in transition-metal-catalyzed coupling processes. This bench-stable derivative offers high solubility in aqueous and polar organic solvents, facilitating integration into synthetic workflows for probe development and targeted labeling.

Application

4-Borono-2-nitrobenzoic acid serves as a versatile building block for the synthesis of boron-containing heterocycles and bioactive molecules. Its ortho-nitro and carboxylic acid functionalities enable directed metalation and selective functionalization, while the boronic acid group facilitates Suzuki-Miyaura coupling under mild conditions. The compound exhibits good bench stability and is compatible with common protecting group strategies, making it well-suited for iterative synthetic sequences in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Tondi, Donatella; Calo, Samuele; Shoichet, Brian K.; Costi, Maria Paola Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 11 p. 3416 - 3419

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

Quality Control

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Computational Chemistry Data

  • TPSA   120.9
  • LogP   -1.0272
  • H_Acceptors   5
  • H_Donors   3
  • Rotatable_Bonds   3

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