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CS-W001157 4
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(5-Cyano-2-methylphenyl)boronic acid

  • CAS No. 867333-43-5

  • Cat. No. CS-W018968
  • Purity≥96%
  • MDL No.MFCD17015778

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

(5-Cyano-2-methylphenyl)boronic acid|CS-W018968

Structure of 867333-43-5

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General Information

  • CAS No. 867333-43-5
  • Cat. No. CS-W018968
  • Purity ≥96%
  • MDL No. MFCD17015778
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BNO₂
  • Molecular Weight 160.97
  • Synonym(s) Boronic acid, (5-cyano-2-methylphenyl)-
  • SMILES CC1=C(C=C(C=C1)C#N)B(O)O

Description

This boronic acid features a cyano group ortho to the boronate, enhancing electrophilicity and enabling efficient cross-coupling. The methyl substituent provides steric control and improves solubility in organic media. Bench-stable under standard conditions, it integrates readily into Suzuki-Miyaura reactions for aryl-aryl bond formation.

Application

(5-Cyano-2-methylphenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient construction of biaryl scaffolds with high functional group tolerance. The nitrile and methyl groups provide orthogonal reactivity for downstream derivatization, while the boronic acid moiety offers excellent bench stability and ease of purification. This compound facilitates access to substituted heterocycles and complex architectures relevant to medicinal chemistry and materials science.

Synthesis

  • Route1
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      121-43-7
    • In-stock
      2-Bromo-4-cyanotoluene|CS-W003347
      42872-74-2
    • ~%
    • In-stock
      (5-Cyano-2-methylphenyl)boronic acid|CS-W018968
      867333-43-5

    References

    • Zhong, Zhenlin; Anslyn, Eric V. Journal of the American Chemical Society, 2002 , vol. 124, # 31 p. 9014 - 9015

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   64.25
  • LogP   -0.4535
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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