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

Name: tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate
Brand: ChemScene
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CAS No. 1072944-96-7
Cat. No. CS-0040989
Purity≥95%
MDL No.None

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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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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.

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

Computational Chemistry Data

TPSA 49.69
LogP 3.7237
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 1

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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Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

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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

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