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(5-Cyanobenzofuran-2-yl)boronic acid

  • CAS No. 331833-83-1

  • Cat. No. CS-0044999
  • Purity≥97%
  • MDL No.MFCD18383022

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

(5-Cyanobenzofuran-2-yl)boronic acid|CS-0044999

Structure of 331833-83-1

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General Information

  • CAS No. 331833-83-1
  • Cat. No. CS-0044999
  • Purity ≥97%
  • MDL No. MFCD18383022
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BNO₃
  • Molecular Weight 186.96
  • Synonym(s) (5-CYANO-1-BENZOFURAN-2-YL)BORONIC ACID
  • SMILES N#CC1=CC=C(OC(B(O)O)=C2)C2=C1

Description

This boronate moiety integrates a cyanobenzofuran scaffold, offering enhanced stability and electron-deficient character for efficient cross-coupling. The para-cyano group enables direct functionalization in Suzuki-Miyaura reactions, delivering complex heterocyclic architectures under standard conditions with minimal decomposition.

Application

(5-Cyanobenzofuran-2-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its benzofuran core provides structural rigidity and metabolic stability, while the nitrile group offers additional handle for downstream functionalization. The boronic acid moiety exhibits excellent bench stability, facile purification, and broad compatibility with diverse functional groups, making it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Friedman; Toyne; Goodby; Hird Journal of Materials Chemistry, 2001 , vol. 11, # 11 p. 2759 - 2772
  • Route2
    • null|null
      121-43-7
    • In-stock
      Benzofuran-5-carbonitrile|CS-0063799
      79002-39-4
    • ~%
    • In-stock
      (5-Cyanobenzofuran-2-yl)boronic acid|CS-0044999
      331833-83-1

    References

    • NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien Patent: WO2011/61168 A1, 2011 ; Location in patent: Page/Page column 54 ; WO 2011/061168 A1
  • Route3

    References

    • Friedman; Toyne; Goodby; Hird Journal of Materials Chemistry, 2001 , vol. 11, # 11 p. 2759 - 2772

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   77.39
  • LogP   -0.01572
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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