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(1-(tert-Butoxycarbonyl)-5-methoxy-1H-indol-2-yl)boronic acid

  • CAS No. 290331-71-4

  • Cat. No. CS-0002271
  • Purity≥98%
  • MDL No.MFCD04039006

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

(1-(tert-Butoxycarbonyl)-5-methoxy-1H-indol-2-yl)boronic acid|CS-0002271

Structure of 290331-71-4

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General Information

  • CAS No. 290331-71-4
  • Cat. No. CS-0002271
  • Purity ≥98%
  • MDL No. MFCD04039006
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BNO₅
  • Molecular Weight 291.11
  • Synonym(s) 1-(Tert-Butoxycarbonyl)-5-Methoxy-1H-Indol-2-Ylboronic Acid
  • SMILES O=C(N1C(B(O)O)=CC2=C1C=CC(OC)=C2)OC(C)(C)C

Application

(1-(tert-Butoxycarbonyl)-5-methoxy-1H-indol-2-yl)boronic acid serves as a stable, bench-ready building block for the construction of indole-based scaffolds in medicinal chemistry and materials science. Its boronic acid functionality enables efficient Suzuki-Miyaura cross-coupling reactions under mild conditions, while the tert-butoxycarbonyl group provides orthogonal protection for the indole nitrogen. The methoxy substituent enhances solubility and modulates electronic properties, supporting diverse downstream functionalization.

Synthesis

  • Route1

    References

    • Mizuta, Masahiro; Seio, Kohji; Miyata, Kenichi; Sekine, Mitsuo Journal of Organic Chemistry, 2007 , vol. 72, # 14 p. 5046 - 5055
  • Route2
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      5419-55-6
    • In-stock
      tert-Butyl 5-methoxy-1H-indole-1-carboxylate|CS-0187679
      99275-47-5
    • ~%
    • In-stock
      (1-(tert-Butoxycarbonyl)-5-methoxy-1H-indol-2-yl)boronic acid|CS-0002271
      290331-71-4

    References

    • NOVARTIS AG; ATKINSON, Benjamin; BEATTIE, David; CULSHAW, Andrew James; DALE, James; DEVEREUX, Nicholas James; MCKENNA, Jeffrey Patent: WO2011/92293 A2, 2011 ; Location in patent: Page/Page column 86 ; WO 2011/092293 A1
  • Route3

    References

    • De Koning, Charles B.; Michael, Joseph P.; Rousseau, Amanda L. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 11 p. 1705 - 1713

Safety Information

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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 : P233-P260-P261-P264-P271-P280-P302+P352-P304+P340-P340-P362-P403-P405-P501

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Computational Chemistry Data

  • TPSA   80.92
  • LogP   1.1129
  • H_Acceptors   6
  • H_Donors   2
  • Rotatable_Bonds   2

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