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

Name: 2-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 458532-82-6
Cat. No. CS-W012246
Purity≥95%
MDL No.MFCD06798252

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2-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W012246

Structure of 458532-82-6

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General Information

CAS No. 458532-82-6
Cat. No. CS-W012246
Purity ≥95%
MDL No. MFCD06798252
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅BBrNO₂
Molecular Weight 283.96
Synonym(s) 2-Bromo-4-pyridylboronic Acid Pinacol Ester
SMILES BrC1=NC=CC(=C1)B2OC(C(O2)(C)C)(C)C

Description

2-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group flanked by a bromopyridine moiety, enabling efficient Suzuki-Miyaura cross-coupling under standard conditions. This bench-stable reagent integrates seamlessly into diverse synthetic sequences, offering precise control over C–C bond formation in complex molecular architectures.

Application

2-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile Suzuki-Miyaura coupling partner, enabling efficient C–C bond formation under mild conditions. The boronate ester group exhibits excellent stability and functional group tolerance, while the bromopyridine moiety facilitates selective cross-coupling. This dual-functional scaffold is ideal for constructing biaryl motifs in pharmaceutical and agrochemical synthesis, offering reliable reactivity and straightforward purification.

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 31.35
LogP 2.1433
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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

CAS No. 458532-82-6

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