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

Name: 2-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 532391-31-4
Cat. No. CS-W012897
Purity≥97%
MDL No.MFCD05663507

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2-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W012897

Structure of 532391-31-4

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General Information

CAS No. 532391-31-4
Cat. No. CS-W012897
Purity ≥97%
MDL No. MFCD05663507
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈BNO₃
Molecular Weight 235.09
Synonym(s) 2-Methoxy pyridine -3-yl boronic acid pinacol ester
SMILES COC1=NC=CC=C1B1OC(C)(C)C(C)(C)O1

Description

2-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling under mild conditions. The electron-rich pyridine core enhances reactivity, while the tetramethyl-substituted dioxaborolane imparts stability and moisture tolerance. This compound integrates readily into complex molecular architectures during synthetic campaigns.

Application

2-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pyridylborane moiety enables efficient C–C bond formation under mild conditions, while the ortho-methoxy group provides electronic modulation and enhances solubility. Bench-stable and compatible with a broad range of functional groups, it facilitates the construction of substituted heterocycles and complex scaffolds in medicinal chemistry and materials synthesis.

Synthesis

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  532391-31-4
References
- Organic Letters, , vol. 15, # 6 p. 1346 - 1349

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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Computational Chemistry Data

TPSA 40.58
LogP 1.3894
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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

CAS No. 532391-31-4

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