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CS-W001157 4
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(4-(Cyanomethyl)phenyl)boronic acid

  • CAS No. 91983-26-5

  • Cat. No. CS-W016144
  • Purity≥97%
  • MDL No.MFCD01632200

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

(4-(Cyanomethyl)phenyl)boronic acid|CS-W016144

Structure of 91983-26-5

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General Information

  • CAS No. 91983-26-5
  • Cat. No. CS-W016144
  • Purity ≥97%
  • MDL No. MFCD01632200
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BNO₂
  • Molecular Weight None
  • Synonym(s) 4-(Cyanomethyl)benzeneboronic Acid (contains varying amounts of Anhydride)
  • SMILES OB(O)C1=CC=C(CC#N)C=C1

Description

This boronate moiety integrates a cyanomethyl group at the para position, enhancing electronic withdrawal and improving stability under standard conditions. The arylboronic acid functionality enables reliable cross-coupling reactions in synthetic workflows.

Application

(4-(Cyanomethyl)phenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl scaffolds with retained nitrile functionality. The cyanomethyl group offers synthetic handle potential for downstream transformations, while the boronic acid moiety provides excellent bench stability and compatibility with diverse reaction conditions. Its predictable reactivity and ease of purification make it a practical choice for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Davison, Joshua Zwick; Jones, Winton Dennis; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael Patent: US2003/225266 A1, 2003 ; Location in patent: Page 23 ;
  • Route2
    • In-stock
      (4-(Bromomethyl)phenyl)boronic acid|CS-W000960
      68162-47-0
    • null|null
      151-50-8
    • ~%
    • In-stock
      (4-(Cyanomethyl)phenyl)boronic acid|CS-W016144
      91983-26-5

    References

    • Tetrahedron, , vol. 19, p. 821 - 826

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+H312+H332-H315-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   64.25
  • LogP   -0.56752
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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