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CS-W001157 4
Total: USD 88.00

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

  • CAS No. 171364-82-2

  • Cat. No. CS-0030567
  • Molecule weight229.08
  • Purity≥98%
  • MDL No.MFCD03093897

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

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile|CS-0030567

Structure of 171364-82-2

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General Information

  • CAS No. 171364-82-2
  • Cat. No. CS-0030567
  • Purity ≥98%
  • MDL No. MFCD03093897
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆BNO₂
  • Molecular Weight 229.08
  • Synonym(s) 4-Cyanophenylboronic Acid Pinacol Ester
  • SMILES N#CC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile features a boronate ester group paired with a para-cyano substituent, enabling efficient Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety ensures excellent stability and moisture tolerance under standard conditions. This combination delivers reliable coupling performance in complex molecule synthesis.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile serves as a robust boronate building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. The tetramethyl-substituted dioxaborolane moiety ensures excellent stability, ease of handling, and compatibility with diverse functional groups. Its nitrile substituent provides a versatile handle for downstream transformations, making it a practical choice for constructing biaryl scaffolds and complex heterocycles in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Organic Letters, , vol. 4, # 4 p. 541 - 543
  • Route2
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • null|null
      22092-92-8
    • null|null
      2252-32-6
    • ~55%
    • In-stock
      4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile|CS-0030567
      171364-82-2

    References

    • WO2014/9169 A1, ; Page/Page column 53-54; 67-68 ;
  • Route3
    • null|null
      2252-32-6
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~76%
    • In-stock
      4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile|CS-0030567
      171364-82-2

    References

    • Organic Letters, , vol. 5, # 24 p. 4635 - 4638

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   1.85748
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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