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

CAS No. 2152673-80-6
Cat. No. CS-0369276
Purity≥95%
MDL No.MFCD34182898

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2,6-Bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0369276

Structure of 2152673-80-6

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Description

This pyridine-based boronate ester integrates a 2,6-bis(benzyloxy) substitution pattern with a sterically protected tetramethyl-dioxaborolane group, enabling stable coupling in Suzuki-Miyaura reactions. The benzyloxy moieties provide enhanced solubility and protection against hydrolysis, while the dioxaborolane unit facilitates efficient transmetalation under mild conditions.

Application

2,6-Bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyridine core enables transition-metal-catalyzed coupling with aryl and vinyl halides under mild conditions. The benzyloxy groups provide orthogonal protection for phenolic functionalities, offering stability during reaction setup and selective deprotection in late-stage synthesis. Its bench-stable nature and compatibility with diverse functional groups make it ideal for complex molecule assembly in medicinal chemistry and materials science workflows.

General Information

CAS No. 2152673-80-6
Cat. No. CS-0369276
Purity ≥95%
MDL No. MFCD34182898
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₅H₂₈BNO₄
Molecular Weight 417.31
Synonym(s) 2,6-bis(phenylmethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Pyridine
SMILES CC1(C)C(C)(C)OB(C2=CC=C(OCC3=CC=CC=C3)N=C2OCC4=CC=CC=C4)O1

Computational Chemistry Data

TPSA 49.81
LogP 4.5388
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 7

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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

CAS No. 2152673-80-6

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