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tert-Butyl 6-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

  • CAS No. 1218790-24-9

  • Cat. No. CS-0063940
  • Molecule weight377.67
  • Purity≥98%
  • MDL No.None

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

tert-Butyl 6-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate|CS-0063940

Structure of 1218790-24-9

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General Information

  • CAS No. 1218790-24-9
  • Cat. No. CS-0063940
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₉H₂₅BClNO₄
  • Molecular Weight 377.67
  • Synonym(s) 1-BOC-6-chloroindole-3-boronic acid,pinacol ester
  • SMILES O=C(N1C=C(B2OC(C)(C)C(C)(C)O2)C3=C1C=C(Cl)C=C3)OC(C)(C)C

Description

tert-Butyl 6-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate features a boronate ester group enabling reliable Suzuki-Miyaura coupling, paired with a chlorine substituent for orthogonal reactivity. This bench-stable, moisture-tolerant building block integrates efficiently into complex heterocycles and biaryl architectures under standard conditions.

Application

tert-Butyl 6-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate serves as a versatile boron-containing building block for palladium-catalyzed cross-coupling reactions. The 6-chloroindole moiety enables selective functionalization via Suzuki-Miyaura coupling, while the protected indole nitrogen and stable boronate group offer excellent bench stability and compatibility with diverse reaction conditions. This reagent facilitates efficient access to substituted indole scaffolds commonly found in medicinal chemistry and agrochemical research.

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   49.69
  • LogP   4.3771
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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