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CS-W001157 4
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2-Aminobenzeneboronic acid

  • CAS No. 5570-18-3

  • Cat. No. CS-W000948
  • Purity≥95%
  • MDL No.MFCD01074645

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

2-Aminobenzeneboronic acid|CS-W000948

Structure of 5570-18-3

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General Information

  • CAS No. 5570-18-3
  • Cat. No. CS-W000948
  • Purity ≥95%
  • MDL No. MFCD01074645
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈BNO₂
  • Molecular Weight 136.94
  • Synonym(s) N'-[(1Z)-(2,5-dimethoxyphenyl)methylidene]-2-[(4-methylphenyl)amino]acetohydrazide (non-preferred name)
  • SMILES OB(c1ccccc1N)O

Description

2-Aminobenzeneboronic acid features a boronate moiety paired with an ortho-amino group, enabling efficient coupling in Suzuki-Miyaura reactions. This bifunctional architecture supports rapid diversification of aryl scaffolds under mild conditions, particularly valuable in medicinal chemistry and materials synthesis.

Application

2-Aminobenzeneboronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-amino and boronic acid functionalities provide complementary reactivity for sequential transformations and facilitate purification via crystallization or chromatography. The compound exhibits good bench stability and functional group tolerance, making it suitable for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Groziak; Ganguly; Robinson Journal of the American Chemical Society, 1994 , vol. 116, # 17 p. 7597 - 7605
  • Route2

    References

    • EP726936 B1, ;
  • Route3

    References

    • Herrbach, Audrey; Marinetti, Angela; Baudoin, Olivier; Guenard, Daniel; Gueritte, Francoise Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4897 - 4905

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   66.48
  • LogP   -1.0514
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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