2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Name: 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 325142-95-8
Cat. No. CS-W006744
Purity≥97%
MDL No.MFCD11617853

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2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W006744

Structure of 325142-95-8

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Description

This boronate-functionalized pyridine features a sterically protected tetramethylboronate group, enabling stable coupling under standard Suzuki-Miyaura conditions. The 2,6-dimethyl substitution enhances solubility and minimizes aggregation, while the electron-deficient pyridine ring facilitates efficient cross-coupling with aryl halides.

Application

2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. The sterically protected boronate group exhibits excellent stability under ambient conditions and resists protodeboronation, enabling reliable coupling with aryl and heteroaryl halides. Its pyridine core facilitates downstream functionalization, while the 2,6-dimethyl substitution enhances solubility and minimizes undesired side reactions. This reagent functions effectively in diverse synthetic workflows requiring selective C–C bond formation.

General Information

CAS No. 325142-95-8
Cat. No. CS-W006744
Purity ≥97%
MDL No. MFCD11617853
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₂
Molecular Weight 233.12
Synonym(s) 2,6-DIMETHYLPYRIDINE-4-BORONIC ACID, PINACOL ESTER
SMILES CC1(C)C(C)(C)OB(C2=CC(C)=NC(C)=C2)O1

Computational Chemistry Data

TPSA 31.35
LogP 1.99764
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 Pyridine compounds

Key Words

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2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

CAS No. 325142-95-8

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