651358-83-7

Basic information

• Product Name: 6-Bromopyridine-2-boronic acid pinacol ester
• Synonyms: 2-BROMO-6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE;6-BROMOPYRIDINE-2-BORONIC ACID PINACOL ESTER;6-Bromopyridine-2-boronic...;2-Bromopyridine-6-boronic acid pinacol ester;2-broMo-6-(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine;6-Bromopyridine-2-boronic acid picol ester
• CAS NO: 651358-83-7
• Molecular Formula: C₁₁H₁₅BBrNO₂
• Molecular Weight: 283.96
• EINECS: 145-896-5
• Mol File: 651358-83-7.mol

Chemical Properties

• Melting Point: 125-127℃
• Boiling Point: 354.7 °C at 760 mmHg
• Flash Point: 168.3 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 6.71E-05mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Toluene
• PKA: 0.82±0.19(Predicted)
• CAS DataBase Reference: 6-Bromopyridine-2-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromopyridine-2-boronic acid pinacol ester(651358-83-7)
• EPA Substance Registry System: 6-Bromopyridine-2-boronic acid pinacol ester(651358-83-7)

Safety Data

• Hazard Codes: T
• Statements: 36/37/38-36-25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN2811
• Hazardous Substances Data: 651358-83-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-Bromopyridine-2-boronic acid pinacol ester is used as a reagent in organic synthesis for its ability to participate in Suzuki-Miyaura cross-coupling reactions, facilitating the formation of carbon-carbon bonds and the creation of complex molecular structures.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-Bromopyridine-2-boronic acid pinacol ester is utilized as a building block for the synthesis of various biologically active molecules and pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Drug Development:
6-Bromopyridine-2-boronic acid pinacol ester is employed in the development of new drugs, leveraging its reactivity and stability to create compounds with desired pharmacological properties, thus advancing the discovery and design of novel therapeutic agents.
Used in Agrochemicals:
6-Bromopyridine-2-boronic acid pinacol ester is also used in the development of agrochemicals, where its chemical properties can be harnessed to create new pesticides or other agricultural chemicals that can improve crop protection and yield.
Used in Chemical Reactions and Mechanisms Study:
6-Bromopyridine-2-boronic acid pinacol ester serves as a valuable tool in the study of chemical reactions and mechanisms in organic chemistry, providing insights into the behavior of boronic esters and their role in cross-coupling reactions.

InChI:InChI=1/C11H15BBrNO2/c1-10(2)11(3,4)16-12(15-10)8-6-5-7-9(13)14-8/h5-7H,1-4H3

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 193344-39-7 2-bromo-6-(4-methoxyphenyl)pyridine 
• 27992-32-1 6-bromo-2-hydroxypyridine 
• 106047-28-3 6-bromo-2-(3-pyridyl)pyridine 

Relevant articles and documents

Synthesis of novel halopyridinylboronic acids and esters. Part 4: Halopyridin-2-yl-boronic acids and esters are stable, crystalline partners for classical Suzuki cross-coupling

This paper describes some methods for the synthesis and the isolation of novel 5 or 6-halopyridin-2-yl-boronic acids and esters 3, 4, 7. These compounds are prepared via a regioselective halogen-metal exchange using n-butyllithium and subsequent quenching with triisopropylborate starting from appropriate dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with arylhalides and authorise a strategy to produce new pyridines libraries.