452972-12-2

Basic information

• Product Name: 2-BROMO-3-PYRIDINEBORONIC ACID PINACOL ESTER
• Synonyms: 2-BROMO-3-PYRIDINEBORONIC ACID PINACOL ESTER;2-BROMO-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE;2-BROMOPYRIDINE-3-BORONIC ACID PINACOL ESTER;2-Bromopyridine-3-boronic acid pinacol ester, Technical, 90%;REF DUPL: 2-Bromopyridine-3-boronic acid pinacol ester;2-Bromopyridin-3-ylboronic acid pinacol ester;2-(2-Bromo-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-Bromo-3-pyridylboronic Acid Pinacol Ester;2-BroMo-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine2
• CAS NO: 452972-12-2
• Molecular Formula: C₁₁H₁₅BBrNO₂
• Molecular Weight: 283.96
• EINECS: 279-594-0
• Product Categories: Boronic acid
• Mol File: 452972-12-2.mol

Chemical Properties

• Melting Point: 28 °C
• Boiling Point: 353.9 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.329 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.08E-05mmHg at 25°C
• Refractive Index: 1.527
• Solubility: soluble in Toluene
• PKA: 0.78±0.12(Predicted)
• CAS DataBase Reference: 2-BROMO-3-PYRIDINEBORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-3-PYRIDINEBORONIC ACID PINACOL ESTER(452972-12-2)
• EPA Substance Registry System: 2-BROMO-3-PYRIDINEBORONIC ACID PINACOL ESTER(452972-12-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 452972-12-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-3-pyridineboronic acid pinacol ester is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique reactivity and ability to form carbon-carbon and carbon-heteroatom bonds make it an essential component in the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Bromo-3-pyridineboronic acid pinacol ester is utilized as a building block for the synthesis of agrochemicals, such as pesticides and herbicides. Its versatility in forming different types of chemical bonds allows for the creation of novel and effective agrochemicals that can address various agricultural challenges.
Used in Materials Science:
2-Bromo-3-pyridineboronic acid pinacol ester is employed in materials science for the development of new materials with specific properties. Its ability to form carbon-carbon and carbon-heteroatom bonds enables the synthesis of advanced materials with applications in various fields, such as electronics, energy storage, and nanotechnology.
Used in Organic Synthesis:
As a versatile boronic acid ester derivative, 2-Bromo-3-pyridineboronic acid pinacol ester is widely used in organic synthesis for the formation of complex organic molecules. Its reactivity and stability make it a valuable tool for chemists and researchers in the synthesis of various organic compounds with potential applications in different industries.

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

Upstream product

• 109-04-6 2-bromo-pyridine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13534-89-9 2,3-dibromopyridine 
• 39856-58-1 3-amino-2-bromopyridine 
• 4214-75-9 2-amino-3-nitropyridine 
• 19755-53-4 2-bromo-3-nitropyridine 

Downstream Products

• 1028424-68-1 (Z)-2-bromo-3-(2-(2-bromopyridin-3-yl)-2-phenylvinyl)pyridine 
• 1028424-74-9 C₁₈H₁₁Br₂N₃O₂ 
• 1028424-75-0 C₁₈H₁₁Br₂ClN₂ 
• 1028424-76-1 C₂₀H₁₆Br₂N₂O 
• 1028424-81-8 C₁₉H₁₄Br₂N₂ 

Relevant articles and documents

Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters

This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4, 7, 10, 13, 15. These compounds are prepared taking into account a regioselective halogen-metal exchange using nBuLi or a regioselective ortho-lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pb-catalyzed coupling with a range of arylhalides and authorize a strategy to produce new pyridines libraries.