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(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid

  • CAS No. 1000068-25-6

  • Cat. No. CS-0002213
  • Molecule weight279.07
  • Purity≥95%
  • MDL No.MFCD11109421

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

(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid|CS-0002213

Structure of 1000068-25-6

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General Information

  • CAS No. 1000068-25-6
  • Cat. No. CS-0002213
  • Purity ≥95%
  • MDL No. MFCD11109421
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅BFNO₄
  • Molecular Weight 279.07
  • Synonym(s) N-Boc-4-Fluoro-1H-indol-2-ylboronic acid
  • SMILES O=C(OC(C)(C)C)N1C(B(O)O)=CC2=C1C=CC=C2F

Description

This boronate moiety integrates a fluoroindole scaffold with a tert-butyl carbamate-protected amine, enabling stable coupling in Suzuki-Miyaura reactions. The electron-deficient arylboronic acid features enhanced shelf life and moisture tolerance, simplifying handling in synthetic workflows.

Application

(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. The Boc-protected indole core enables orthogonal functionalization in complex molecule synthesis, while the fluorine substituent enhances metabolic stability and modulates electronic properties. Its excellent functional group tolerance and ease of purification make it ideal for constructing pharmaceutically relevant indole scaffolds in medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • SANOFI-AVENTIS Patent: WO2008/14186 A1, 2008 ; Location in patent: Page/Page column 46 ; WO 2008/014186 A1

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   1.2434
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   1

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