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(5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid

  • CAS No. 475102-13-7

  • Cat. No. CS-0002263
  • Molecule weight339.98
  • Purity≥97%
  • MDL No.MFCD03701683

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

(5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid|CS-0002263

Structure of 475102-13-7

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General Information

  • CAS No. 475102-13-7
  • Cat. No. CS-0002263
  • Purity ≥97%
  • MDL No. MFCD03701683
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅BBrNO₄
  • Molecular Weight 339.98
  • Synonym(s) T56 BNJ BVOX1&1&1 CBQQ GE [WLN]
  • SMILES O=C(N1C(B(O)O)=CC2=C1C=CC(Br)=C2)OC(C)(C)C

Description

This boronate moiety integrates a bromo-substituted indole scaffold with a tert-butoxycarbonyl-protected amine, offering a bench-stable, moisture-tolerant platform for palladium-catalyzed cross-coupling reactions. The protected nitrogen and electron-deficient aryl boron handle enable selective functionalization in complex molecular architectures.

Application

(5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation with aryl and vinyl halides. The boronic acid functionality offers excellent bench stability and compatibility with diverse reaction conditions, while the tert-butoxycarbonyl group provides orthogonal protection for the indole nitrogen. This combination facilitates sequential functionalization and simplifies purification, making it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

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 : 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   1.8668
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   1

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