2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Name: 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
Brand: ChemScene
Availability: InStock
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CAS No. 876922-75-7
Cat. No. CS-0108810
Purity≥98%
MDL No.MFCD22418301

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2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline|CS-0108810

Structure of 876922-75-7

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Description

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline is a bench-stable boronate reagent featuring a sterically protected boryl group attached to a quinoline scaffold. This configuration enables efficient Suzuki-Miyaura cross-coupling under mild conditions, delivering functionalized quinoline derivatives with high regioselectivity and minimal protodeboronation.

Application

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline serves as a robust boronate building block for palladium-catalyzed cross-coupling reactions. Its quinoline scaffold offers enhanced stability and favorable electronic properties, enabling efficient Suzuki-Miyaura coupling with aryl, vinyl, and heteroaryl halides. The tetramethylboronate group ensures excellent shelf life, low toxicity, and ease of purification, making it ideal for modular synthesis of biologically relevant heterocycles and advanced pharmaceutical intermediates.

General Information

CAS No. 876922-75-7
Cat. No. CS-0108810
Purity ≥98%
MDL No. MFCD22418301
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₀BNO₂
Molecular Weight 269.15
Synonym(s) 2-Methyl-quinoline-5-boronic acid pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=C3C=CC(C)=NC3=CC=C2)O1

Computational Chemistry Data

TPSA 31.35
LogP 2.84242
H_Acceptors 3
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-H320-H335
Precautionary Statements : P261-P280-P302+P352

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Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

CAS No. 876922-75-7

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