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CS-W001157 4
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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile

  • CAS No. 238088-16-9

  • Cat. No. CS-0174435
  • Molecule weight195.07
  • Purity≥98%
  • MDL No.None

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

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile|CS-0174435

Structure of 238088-16-9

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General Information

  • CAS No. 238088-16-9
  • Cat. No. CS-0174435
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₈BNO₂
  • Molecular Weight 195.07
  • Synonym(s) 3-Cyano-1-propylboronic acid pinacol ester
  • SMILES CC1(C(C)(OB(O1)CCCC#N)C)C

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile features a boronate ester group paired with a terminal nitrile, enabling efficient cross-coupling reactions under mild conditions. The tetramethyl-substituted dioxaborolane enhances stability and resistance to hydrolysis, while the butanenitrile chain provides a polar handle for downstream functionalization. This combination delivers robust performance in Suzuki-Miyaura coupling workflows.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile serves as a versatile boron-containing building block in Suzuki-Miyaura cross-coupling reactions. The nitrile group provides a stable, polar handle compatible with various functional groups, enabling efficient incorporation into complex molecular architectures. Its bench-stable dioxaborolane moiety facilitates reliable coupling under mild conditions, making it ideal for constructing biaryl and heterocyclic scaffolds in medicinal chemistry and materials science workflows.

Synthesis

  • Route1
    • null|null
      143-33-9
    • In-stock
      2-(3-Bromopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174363
      124215-44-7
    • ~92%
    • In-stock
      4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile|CS-0174435
      238088-16-9

    References

    • Man, Hon-Wah; Hiscox, William C.; Matteson, Donald S. Organic Letters, 1999 , vol. 1, # 3 p. 379 - 381
  • Route2
    • null|null
      109-75-1
    • null|null
      25015-63-8
    • ~15%
    • In-stock
      4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile|CS-0174435
      238088-16-9

    References

    • Yamamoto, Yasunori; Fujikawa, Rhyou; Umemoto, Tomokazu; Miyaura, Norio Tetrahedron, 2004 , vol. 60, # 47 p. 10695 - 10700
  • Route3

    References

    • Organic Letters, , vol. 1, # 3 p. 379 - 381

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

Quality Control

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Computational Chemistry Data

  • TPSA   42.25
  • LogP   2.38238
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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