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CS-W001157 4
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2-(Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 796851-30-4

  • Cat. No. CS-0174206
  • Purity≥98%
  • MDL No.None

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

2-(Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174206

Structure of 796851-30-4

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General Information

  • CAS No. 796851-30-4
  • Cat. No. CS-0174206
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₇BO₃
  • Molecular Weight 244.09
  • Synonym(s) 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran
  • SMILES CC1(C(C)(OB(O1)C2=COC3=CC=CC=C23)C)C

Description

This boronate ester integrates a benzofuran-3-yl moiety with a sterically shielded tetramethyl-1,3,2-dioxaborolane group, delivering enhanced stability and compatibility in Suzuki-Miyaura coupling reactions. The electron-rich aromatic system facilitates efficient palladium-catalyzed cross-coupling under standard conditions, enabling rapid access to biaryl architectures in medicinal chemistry and materials synthesis.

Application

2-(Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its tetramethyl-substituted dioxaborolane moiety enhances air and moisture stability while enabling efficient coupling with aryl and heteroaryl halides. The benzofuran scaffold provides a versatile core for constructing biologically relevant molecules and functional materials, with excellent functional group tolerance and straightforward purification via flash chromatography.

Synthesis

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    • In-stock
      2-(Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174206
      796851-30-4

    References

    • US2009/54454 A1, ; Page/Page column 17 ; US 20090054454 A1
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    • In-stock
      2-(Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174206
      796851-30-4
    • In-stock
      2-(Benzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0091643
      402503-13-3

    References

    • Journal of the American Chemical Society, , vol. 128, # 49 p. 15552 - 15553
  • Route3

    References

    • Advanced Synthesis and Catalysis, , vol. 352, # 10 p. 1662 - 1666

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   31.6
  • LogP   2.732
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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