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CS-W001157 4
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(1-(Tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid

  • CAS No. 317830-84-5

  • Cat. No. CS-0175399
  • Purity≥95%
  • MDL No.None

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

(1-(Tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid|CS-0175399

Structure of 317830-84-5

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General Information

  • CAS No. 317830-84-5
  • Cat. No. CS-0175399
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆BNO₄
  • Molecular Weight 261.08
  • Synonym(s) 1-(tert-butoxycarbonyl)-1H-indole-5-boronic acid
  • SMILES CC(C)(OC(N1C=CC2=CC(B(O)O)=CC=C21)=O)C

Description

This boronate moiety integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under standard conditions. The tert-butoxycarbonyl-protected indole scaffold offers enhanced stability and compatibility with diverse reaction environments.

Application

(1-(Tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. The Boc-protected indole moiety offers enhanced stability and compatibility with diverse reaction conditions, enabling efficient access to functionalized indole scaffolds. Its orthogonal reactivity facilitates late-stage diversification in medicinal chemistry and materials synthesis, while the boronic acid group supports straightforward purification and robust coupling performance.

Synthesis

  • Route1

    References

    • PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; FURUYA, Takeru; TANG, Pingping Patent: WO2010/59943 A2, 2010 ; Location in patent: Page/Page column 85 ;
  • Route2
    • tert-Butyl 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-1-carboxylate|CS-0805869
      1167418-11-2
    • ~53%
    • In-stock
      (1-(Tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid|CS-0175399
      317830-84-5

    References

    • Furuya, Takeru; Ritter, Toblas Organic Letters, 2009 , vol. 11, # 13 p. 2860 - 2863
  • Route3

    References

    • Molander, Gary A.; Trice, Sarah L. J.; Kennedy, Steven M. Organic Letters, 2012 , vol. 14, # 18 p. 4814 - 4817,4

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

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Computational Chemistry Data

  • TPSA   71.69
  • LogP   1.1043
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   1

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