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

Name: 3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 452972-13-3
Cat. No. CS-0041166
Purity≥97%
MDL No.MFCD06798248

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3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0041166

Structure of 452972-13-3

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Description

3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group paired with a bromopyridine handle, enabling efficient Suzuki-Miyaura coupling under standard conditions. The tetramethyl-substituted dioxaborolane enhances stability and solubility in organic media. This bifunctional building block integrates seamlessly into complex heterocyclic architectures, streamlining the synthesis of conjugated systems for pharmaceutical and materials applications.

Application

3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile Suzuki-Miyaura coupling building block, combining a readily displaced bromide with a stable boronate ester. Its orthogonal reactivity enables sequential functionalization in complex molecule assembly. The tetramethylcyclopentadienone-derived boronate offers excellent bench stability, minimal protodeboronation, and compatibility with diverse reaction conditions. Ideal for constructing biaryl scaffolds and heterocyclic frameworks in medicinal chemistry and materials science workflows.

General Information

CAS No. 452972-13-3
Cat. No. CS-0041166
Purity ≥97%
MDL No. MFCD06798248
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅BBrNO₂
Molecular Weight 283.96
Synonym(s) 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE
SMILES CC1(C)C(C)(C)OB(C2=CN=CC(Br)=C2)O1

Computational Chemistry Data

TPSA 31.35
LogP 2.1433
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 : H315-H319
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 Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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

CAS No. 452972-13-3

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