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tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate

  • CAS No. 1072944-96-7

  • Cat. No. CS-0040989
  • Purity≥95%
  • MDL No.None

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

tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate|CS-0040989

Structure of 1072944-96-7

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General Information

  • CAS No. 1072944-96-7
  • Cat. No. CS-0040989
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₉H₂₆BNO₄
  • Molecular Weight 343.23
  • Synonym(s) Tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indole-1-carboxylate
  • SMILES O=C(N1C(B2OC(C)(C)C(C)(C)O2)=CC3=C1C=CC=C3)OC(C)(C)C

Description

tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate features a boronate ester group integrated into an indole scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane ring enhances stability and reactivity, while the tert-butyl carbamate protects the indole nitrogen. This combination delivers reliable functionalization in complex molecule synthesis.

Application

tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The indole-1-carboxylate moiety provides orthogonal protection and facilitates downstream functionalization, while the tetramethylboronate group enables efficient coupling with aryl, heteroaryl, and vinyl halides under mild conditions. Its high stability, compatibility with diverse reaction setups, and ease of purification make it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials synthesis.

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   49.69
  • LogP   3.7237
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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