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CS-W001157 4
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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

  • CAS No. 642494-36-8

  • Cat. No. CS-0038313
  • Purity≥95%
  • MDL No.MFCD07368852

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

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0038313

Structure of 642494-36-8

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General Information

  • CAS No. 642494-36-8
  • Cat. No. CS-0038313
  • Purity ≥95%
  • MDL No. MFCD07368852
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BNO₂
  • Molecular Weight None
  • Synonym(s) Indole-6-boronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CC3=C(C=C2)C=CN3)O1

Description

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole integrates a stable boronate handle at the 6-position of indole, enabling efficient Suzuki-Miyaura cross-coupling. This bench-stable reagent facilitates rapid diversification of indole scaffolds in medicinal chemistry and materials synthesis.

Application

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The stable boronate ester group enables efficient C–C bond formation under mild conditions, facilitating the construction of biaryl and heteroaryl architectures. Its compatibility with diverse functional groups and excellent bench stability make it ideal for iterative synthesis and library generation in medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • Appukkuttan, Prasad; Van Der Eycken, Erik; Dehaen, Wim Synlett, 2003 , # 8 p. 1204 - 1206
  • Route2
    • null|null
      104-92-7
    • In-stock
      tert-Butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole-1-carboxylate|CS-0671845
      777061-38-8
    • ~10%
    • In-stock
      6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0038313
      642494-36-8
    • null|null
      147621-14-5

    References

    • Journal of Organic Chemistry, , vol. 69, # 20 p. 6812 - 6820
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 69, # 20 p. 6812 - 6820

Safety Information

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Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   34.25
  • LogP   2.4671
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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