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1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

  • CAS No. 837392-62-8

  • Cat. No. CS-W021356
  • Purity≥97%
  • MDL No.MFCD05663865

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

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-W021356

Structure of 837392-62-8

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General Information

  • CAS No. 837392-62-8
  • Cat. No. CS-W021356
  • Purity ≥97%
  • MDL No. MFCD05663865
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₀BNO₂
  • Molecular Weight 257.14
  • Synonym(s) 1-Methyl-5-(4
  • SMILES CC1(C)C(C)(C)OB(C2=CC3=C(N(C)C=C3)C=C2)O1

Description

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole is a bench-stable boronate ester featuring a sterically shielded dioxaborolane group attached to an electron-rich indole core. This structure enables efficient Suzuki-Miyaura coupling reactions under mild conditions, facilitating the rapid construction of biaryl architectures in medicinal chemistry and materials synthesis. The tetramethyl-substituted boronate moiety enhances hydrolytic stability and compatibility with aqueous reaction media.

Application

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient palladium-catalyzed coupling with aryl and heteroaryl halides under mild conditions. Its indole core provides a versatile scaffold for medicinal chemistry and materials science applications, offering excellent functional group tolerance and straightforward purification due to low background reactivity.

Synthesis

  • Route1

    References

    • Yamamoto, Eiji; Izumi, Kiyotaka; Horita, Yuko; Ito, Hajime Journal of the American Chemical Society, 2012 , vol. 134, # 49 p. 19997 - 20000
  • Route2
    • In-stock
      5-Bromo-1-methyl-1H-indole|CS-0034511
      10075-52-2
    • null|null
      25015-63-8
    • ~75%
    • In-stock
      1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-W021356
      837392-62-8

    References

    • Stadlwieser, Josef F.; Dambaur, Markus E. Helvetica Chimica Acta, 2006 , vol. 89, # 5 p. 936 - 946
  • Route3

    References

    • Helvetica Chimica Acta, , vol. 89, # 5 p. 936 - 946

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   23.39
  • LogP   2.4775
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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