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CS-W001157 4
Total: USD 88.00

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

  • CAS No. 642494-37-9

  • Cat. No. CS-W022521
  • Purity≥97%
  • MDL No.MFCD08669591

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

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-W022521

Structure of 642494-37-9

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General Information

  • CAS No. 642494-37-9
  • Cat. No. CS-W022521
  • Purity ≥97%
  • MDL No. MFCD08669591
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BNO₂
  • Molecular Weight 243.11
  • Synonym(s) Indole-7-boronic acid pinacol ester
  • SMILES CC1(C)OB(OC1(C)C)C1=CC=CC2=C1NC=C2

Description

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole integrates a stable boronate ester at the 7-position of indole, enabling efficient Suzuki-Miyaura cross-coupling under mild conditions. The tetramethyl dioxaborolane moiety enhances reactivity and shelf stability, while the electron-rich indole core supports diverse functionalization in medicinal chemistry and materials synthesis.

Application

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient C–C bond formation under mild conditions, with excellent stability during storage and handling. It functions reliably in the synthesis of biaryl scaffolds, particularly in constructing substituted indole derivatives used in pharmaceutical and agrochemical research.

Synthesis

  • Route1
    • In-stock
      7-Bromo-1H-indole|CS-W002687
      51417-51-7
    • null|null
      25015-63-8
    • ~52%
    • In-stock
      7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-W022521
      642494-37-9

    References

    • Mentzel, Uffe V.; Tanner, David; Tonder, Janne E. Journal of Organic Chemistry, 2006 , vol. 71, # 15 p. 5807 - 5810
  • Route2

    References

    • Appukkuttan, Prasad; Van Der Eycken, Erik; Dehaen, Wim Synlett, 2003 , # 8 p. 1204 - 1206
  • Route3
    • null|null
      116491-57-7
    • ~%
    • In-stock
      7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-W022521
      642494-37-9

    References

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

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

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