4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline

Name: 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline
Brand: ChemScene
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CAS No. 1035458-54-8
Cat. No. CS-W021993
Purity≥97%
MDL No.MFCD05155221

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4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline|CS-W021993

Structure of 1035458-54-8

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Description

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline integrates a boronate handle with a quinoline scaffold, enabling direct coupling in palladium-catalyzed cross-coupling reactions. The tetramethyl-dioxaborolane moiety ensures high stability and reactivity under standard conditions, while the electron-deficient quinoline ring facilitates efficient functionalization. This compound streamlines access to complex heteroaromatic architectures in medicinal chemistry and materials science.

Application

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline serves as a versatile boron-containing building block in palladium-catalyzed cross-coupling reactions. Its stable boronate ester group enables efficient Suzuki-Miyaura coupling with aryl and heteroaryl halides under mild conditions. The quinoline scaffold provides a rigid, electron-deficient platform suitable for constructing complex heterocyclic architectures in medicinal chemistry and materials science. Bench-stable and readily purified by flash chromatography, it functions reliably in multi-step synthetic sequences requiring functional group tolerance and predictable reactivity.

General Information

CAS No. 1035458-54-8
Cat. No. CS-W021993
Purity ≥97%
MDL No. MFCD05155221
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₈BNO₂
Molecular Weight None
Synonym(s) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
SMILES CC1(C)C(C)(C)OB(C2=CC=NC3=CC=CC=C23)O1

Computational Chemistry Data

TPSA 31.35
LogP 2.534
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-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 Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline

CAS No. 1035458-54-8

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