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CS-W001157 4
Total: USD 88.00

4-Carboxy-2-nitrophenylboronic acid

  • CAS No. 85107-54-6

  • Cat. No. CS-W015086
  • Molecule weight210.94
  • Purity≥95%
  • MDL No.MFCD00448780

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

4-Carboxy-2-nitrophenylboronic acid|CS-W015086

Structure of 85107-54-6

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General Information

  • CAS No. 85107-54-6
  • Cat. No. CS-W015086
  • Purity ≥95%
  • MDL No. MFCD00448780
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BNO₆
  • Molecular Weight 210.94
  • Synonym(s) 4-Carboxy-2-nitrophenylboronicacid
  • SMILES O=C(O)C1=CC=C(B(O)O)C([N+]([O-])=O)=C1

Description

4-Carboxy-2-nitrophenylboronic acid features a boronate group flanked by electron-withdrawing nitro and carboxylic acid functionalities, enhancing its reactivity in Suzuki-Miyaura couplings. This combination delivers high chemoselectivity and stability under standard conditions, enabling efficient incorporation into complex molecular architectures.

Application

4-Carboxy-2-nitrophenylboronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient construction of biaryl scaffolds under mild conditions. The ortho-nitro and carboxylic acid groups provide orthogonal functionality for downstream derivatization, while the boronic acid moiety offers excellent bench stability and compatibility with diverse reaction partners. Its defined regiochemistry facilitates predictable coupling outcomes, making it ideal for synthesizing complex heterocyclic systems and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Journal of the American Chemical Society, , vol. 81, p. 3017 Arkiv foer Kemi, , vol. 10, p. 479,504
  • Route2

    References

    • B: B-Verb.13, 4.7.2.5, page 209 - 219

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

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