5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Name: 5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Brand: ChemScene
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CAS No. 1256358-91-4
Cat. No. CS-0174918
Purity≥98%
MDL No.None

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5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0174918

Structure of 1256358-91-4

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Description

5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole is a bench-stable boronate ester featuring a chlorinated indole core. This structure enables efficient palladium-catalyzed cross-coupling reactions, particularly Suzuki-Miyaura couplings, where the tetramethyl-substituted dioxaborolane moiety enhances solubility and reaction kinetics. The electron-deficient chloro group directs regioselective functionalization.

Application

5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a versatile Suzuki-Miyaura coupling partner, enabling efficient C–C bond formation under mild conditions. The boronate group exhibits high stability, excellent functional group tolerance, and compatibility with diverse reaction substrates. Its indole core provides a privileged scaffold for medicinal chemistry applications, while the chloro substituent allows for orthogonal transformations. Ideal for sequential cross-coupling strategies and modular synthesis of complex heterocyclic architectures.

General Information

CAS No. 1256358-91-4
Cat. No. CS-0174918
Purity ≥98%
MDL No. None
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₇BClNO₂
Molecular Weight 277.55
Synonym(s) 5-Chloroindole-2-boronic acid pinacol ester
SMILES CC1(C(C)(OB(O1)C2=CC3=CC(Cl)=CC=C3N2)C)C

Computational Chemistry Data

TPSA 34.25
LogP 3.1205
H_Acceptors 2
H_Donors 1
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 : H317-H319
Precautionary Statements : P261-P264-P272-P280-P302+P352-P362+P364-P501

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Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Key Words

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5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

CAS No. 1256358-91-4

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