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CS-W001157 4
Total: USD 88.00

Indole-4-boronic acid pinacol ester

  • CAS No. 388116-27-6

  • Cat. No. CS-W019752
  • Purity≥98%
  • MDL No.MFCD08689896

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

Indole-4-boronic acid pinacol ester|CS-W019752

Structure of 388116-27-6

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General Information

  • CAS No. 388116-27-6
  • Cat. No. CS-W019752
  • Purity ≥98%
  • MDL No. MFCD08689896
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BNO₂
  • Molecular Weight None
  • Synonym(s) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
  • SMILES CC1(C)C(C)(C)OB(C2=CC=CC3=C2C=CN3)O1

Description

Indole-4-boronic acid pinacol ester offers a bench-stable, moisture-tolerant platform for Suzuki-Miyaura cross-coupling reactions. This boronate ester integrates seamlessly into complex molecular architectures, enabling efficient C–C bond formation under mild conditions. The indole core provides a privileged scaffold for bioactive molecule synthesis, while the pinacol protection enhances handling and shelf stability.

Application

Indole-4-boronic acid pinacol ester serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. Its robust boronate ester functionality enables efficient C–C bond formation with aryl and vinyl halides under mild conditions, facilitating the construction of biaryl and styryl derivatives. The molecule exhibits excellent functional group tolerance and simplifies purification due to low byproduct formation, making it a practical choice for synthesizing complex heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • LOCUS PHARMACEUTICALS, INC. Patent: WO2008/8059 A1, 2008 ; Location in patent: Page/Page column 81-82 ;
  • Route2

    References

    • GENENTECH, INC.; SUMITOMO CHEMICAL COMPANY, LIMITED Patent: US2012/123122 A1, 2012 ; Location in patent: Page/Page column 13-14 ;
  • Route3

    References

    • SUGEN, INC. Patent: WO2004/76412 A2, 2004 ; Location in patent: Page 96 ; WO 2004/076412 A2

Safety Information

Download SDS
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 : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-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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