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CS-W001157 4
Total: USD 88.00

4-(Cyanomethyl)benzeneboronic acid pinacol ester

  • CAS No. 138500-86-4

  • Cat. No. CS-0052091
  • Purity≥95%
  • MDL No.None

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

4-(Cyanomethyl)benzeneboronic acid pinacol ester|CS-0052091

Structure of 138500-86-4

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General Information

  • CAS No. 138500-86-4
  • Cat. No. CS-0052091
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BNO₂
  • Molecular Weight 243.11
  • Synonym(s) 4-(Cyanomethyl)phenylboronic acid pinacol ester
  • SMILES CC1(C)OB(OC1(C)C)C1=CC=C(CC#N)C=C1

Description

4-(Cyanomethyl)benzeneboronic acid pinacol ester delivers a boronate moiety flanked by a para-cyanoalkyl group, enabling efficient cross-coupling in palladium-catalyzed reactions. The pinacol ester enhances stability and solubility, simplifying handling and storage under standard conditions. This compound integrates seamlessly into complex molecular architectures requiring selective C–C bond formation.

Application

4-(Cyanomethyl)benzeneboronic acid pinacol ester serves as a stable, bench-ready building block for Suzuki-Miyaura coupling reactions. The pinacol boronate ester enhances reagent stability and simplifies purification, while the pendant nitrile group enables downstream transformations such as amidation or reduction. Its compatibility with diverse reaction conditions makes it a practical choice for constructing biaryl architectures and functionalized heterocycles in medicinal chemistry and materials synthesis.

Synthesis

  • Route1
    • In-stock
      2-(4-Iodophenyl)acetonitrile|CS-W005301
      51628-12-7
    • null|null
      25015-63-8
    • ~99%
    • In-stock
      4-(Cyanomethyl)benzeneboronic acid pinacol ester|CS-0052091
      138500-86-4

    References

    • Davison, Joshua Zwick; Jones, Winton Dennis; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael Patent: US2003/225266 A1, 2003 ; Location in patent: Page 23 ;
  • Route2
    • null|null
      1350764-44-1
    • null|null
      25015-63-8
    • ~71%
    • In-stock
      4-(Cyanomethyl)benzeneboronic acid pinacol ester|CS-0052091
      138500-86-4

    References

    • Murata, Miki; Oda, Takeshi; Sogabe, Yosuke; Tone, Hirofumi; Namikoshi, Takeshi; Watanabe, Shinji Chemistry Letters, 2011 , vol. 40, # 9 p. 962 - 963
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 65, # 1 p. 164 - 168

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   42.25
  • LogP   2.05188
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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