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CS-W001157 4
Total: USD 88.00

(3-Cyano-4-methylphenyl)boronic acid

  • CAS No. 911210-49-6

  • Cat. No. CS-0135004
  • Purity≥97%
  • MDL No.MFCD10697414

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

(3-Cyano-4-methylphenyl)boronic acid|CS-0135004

Structure of 911210-49-6

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General Information

  • CAS No. 911210-49-6
  • Cat. No. CS-0135004
  • Purity ≥97%
  • MDL No. MFCD10697414
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BNO₂
  • Molecular Weight 160.97
  • Synonym(s) 3-Cyano-4-methylphenylboronic acid
  • SMILES CC1=CC=C(C=C1C#N)B(O)O

Description

This boronate reagent features a cyano-substituted aryl ring paired with a methyl group at the ortho position, delivering enhanced stability and predictable reactivity in Suzuki-Miyaura cross-coupling. The electron-withdrawing nitrile group modulates electronic density, enabling efficient coupling under mild conditions. Bench-stable and moisture-tolerant, it integrates seamlessly into synthetic workflows requiring precise functionalization of biaryl scaffolds.

Application

(3-Cyano-4-methylphenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-cyano and methyl substituents provide enhanced stability and tunable electronic properties, facilitating downstream functionalization. The boronic acid moiety exhibits excellent bench stability, ease of purification, and compatibility with diverse reaction partners, making it well-suited for the synthesis of substituted biaryls and complex heterocyclic scaffolds in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • SPEEDEL EXPERIMENTA AG Patent: WO2006/103273 A1, 2006 ; Location in patent: Page/Page column 43 ; WO 2006/103273 A1

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
Precautionary Statements : P264-P270-P301+P310-P330-P501

Quality Control

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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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