(2-(Methoxycarbonyl)-1H-indol-5-yl)boronic acid

Name: (2-(Methoxycarbonyl)-1H-indol-5-yl)boronic acid
Brand: ChemScene
Availability: InStock
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CAS No. 284660-86-2
Cat. No. CS-0035811
Purity≥98%
MDL No.MFCD09751354

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(2-(Methoxycarbonyl)-1H-indol-5-yl)boronic acid|CS-0035811

Structure of 284660-86-2

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General Information

CAS No. 284660-86-2
Cat. No. CS-0035811
Purity ≥98%
MDL No. MFCD09751354
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₀BNO₄
Molecular Weight 219.00
Synonym(s) 2-Methoxycarbonylindole-5-boronic acid
SMILES COC(=O)C1=CC2=CC(=CC=C2N1)B(O)O

Description

This boronate moiety integrates a methoxycarbonyl group at the 2-position of an indole scaffold, delivering enhanced stability and solubility. The para-functionalized indole core enables efficient Suzuki-Miyaura coupling under standard conditions, facilitating rapid access to complex heterocyclic architectures in medicinal chemistry and materials science.

Application

(2-(Methoxycarbonyl)-1H-indol-5-yl)boronic acid serves as a versatile building block for the synthesis of biologically relevant indole derivatives via Suzuki-Miyaura cross-coupling. Its boronic acid functionality enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the methoxycarbonyl group provides orthogonal reactivity for downstream transformations. The compound exhibits good bench stability and is readily purified by flash chromatography, facilitating integration into multi-step synthetic sequences for medicinal chemistry and materials applications.

Synthesis

Route1
- In-stock
  
  284660-89-5
- 111-42-2
- ~12%
- In-stock
  
  284660-86-2
References
- Hangauer, David G. Patent: US2008/4241 A1, 2008 ; Location in patent: Page/Page column 140-141 ; US 20080004241 A1

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 82.55
LogP -0.3657
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Key Words

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(2-(Methoxycarbonyl)-1H-indol-5-yl)boronic acid

CAS No. 284660-86-2

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