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CS-W001157 4
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(E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile

  • CAS No. 172512-93-5

  • Cat. No. CS-B1124
  • Purity≥97%
  • MDL No.MFCD19703873

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

(E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile|CS-B1124

Structure of 172512-93-5

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General Information

  • CAS No. 172512-93-5
  • Cat. No. CS-B1124
  • Purity ≥97%
  • MDL No. MFCD19703873
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₈BNO₂
  • Molecular Weight 255.12
  • Synonym(s) 4-Cyano-trans-beta-styrylboronic acidpinacol ester
  • SMILES CC(O1)(C)C(C)(C)OB1/C=C/C2=CC=C(C#N)C=C2

Description

This boronate-functionalized vinylbenzonitrile integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions. The tetramethylborolane moiety ensures high stability and moisture tolerance, while the electron-deficient nitrile group enhances reactivity in transition-metal-catalyzed transformations.

Application

(E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The vinylboronate moiety enables efficient coupling with aryl halides and pseudohalides under mild conditions, while the nitrile group provides a stable, electron-withdrawing handle compatible with diverse downstream transformations. Bench-stable and easily purified, it functions reliably in the construction of conjugated biaryl systems and functionalized heterocycles relevant to medicinal chemistry and materials science.

Synthesis

  • Route1
    • In-stock
      4-Ethynylbenzonitrile|CS-W007419
      3032-92-6
    • null|null
      25015-63-8
    • ~65%
    • In-stock
      (E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile|CS-B1124
      172512-93-5

    References

    • Yasu, Yusuke; Koike, Takashi; Akita, Munetaka Chemical Communications, 2013 , vol. 49, # 20 p. 2037 - 2039

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   3.20288
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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