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

Name: (5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid
Brand: ChemScene
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CAS No. 475102-13-7
Cat. No. CS-0002263
Purity≥97%
MDL No.MFCD03701683

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FedEx Limited Quantities Ground	$0.00
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(5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid|CS-0002263

Structure of 475102-13-7

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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.

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

Computational Chemistry Data

TPSA 71.69
LogP 1.8668
H_Acceptors 5
H_Donors 2
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 Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Key Words

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

CAS No. 475102-13-7

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