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CS-W001157 4
Total: USD 88.00

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile

  • CAS No. 325141-71-7

  • Cat. No. CS-0138342
  • Purity≥97%
  • MDL No.MFCD02179457

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

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile|CS-0138342

Structure of 325141-71-7

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General Information

  • CAS No. 325141-71-7
  • Cat. No. CS-0138342
  • Purity ≥97%
  • MDL No. MFCD02179457
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BNO₂
  • Molecular Weight None
  • Synonym(s) (2-Cyanomethylphenyl)Boronic Acid Pinacol Ester
  • SMILES N#CCC1=CC=CC=C1B2OC(C)(C)C(C)(C)O2

Description

This boronate-functionalized nitrile integrates readily into Suzuki-Miyaura coupling reactions under standard conditions. The tetramethyl-1,3,2-dioxaborolane moiety ensures high stability and compatibility with diverse reaction environments. The acetonitrile group provides a polar handle for downstream derivatization, enhancing utility in synthetic workflows requiring precise functional group placement.

Application

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The nitrile group provides orthogonal reactivity and enhanced solubility, while the tetramethyl-substituted dioxaborolane ensures excellent stability and compatibility with diverse reaction conditions. Ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      19472-74-3
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~75%
    • In-stock
      2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile|CS-0138342
      325141-71-7

    References

    • Rochais, Christophe; Yougnia, Rodrigue; Cailly, Thomas; Sopkova-De Oliveira Santos, Jana; Rault, Sylvain; Dallemagne, Patrick Tetrahedron, 2011 , vol. 67, # 32 p. 5806 - 5810
  • Route2
    • null|null
      19472-74-3
    • null|null
      25015-63-8
    • ~60%
    • null|null
      140-29-4
    • In-stock
      2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile|CS-0138342
      325141-71-7

    References

    • Journal of Organic Chemistry, , vol. 65, # 26 p. 9268 - 9271
  • Route3
    • In-stock
      2-(2-Iodophenyl)acetonitrile|CS-0041514
      40400-15-5
    • null|null
      25015-63-8
    • ~91%
    • null|null
      140-29-4
    • In-stock
      2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile|CS-0138342
      325141-71-7

    References

    • Journal of Organic Chemistry, , vol. 65, # 26 p. 9268 - 9271

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3276
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P233-P260-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-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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