223463-14-7

Basic information

• Product Name: 2-Bromopyridine-5-boronic acid
• Synonyms: 2-BROMO-5-PYRIDINEBORONIC ACID;2-BROMOPYRIDINE-5-BORONIC ACID;2-BROMOPYRIDYL-5-BORONIC ACID;6-BROMOPYRIDINE-3-BORONIC ACID;6-BROMOPYRIDIN-3-YL-3-BORONIC ACID;(6-BROMOPYRIDIN-3-YL)BORONIC ACID;6-BROMO-3-PYRIDINEBORONIC ACID;(6-BROMO-3-PYRIDINYL)-BORONIC ACID
• CAS NO: 223463-14-7
• Molecular Formula: C₅H₅BBrNO₂
• Molecular Weight: 201.81
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Pyridine;Boronic Acids & Esters;Pyridines;Boronic acids;Boronic acid;Organoborons;B (Classes of Boron Compounds);Bromopyridines;Halopyridines;Boronic Acids & Esters;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;alkyl bromide|boric acid
• Mol File: 223463-14-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 161-166 °C
• Boiling Point: 358.2 °C at 760 mmHg
• Flash Point: 170.4 °C
• Appearance: /
• Density: 1.78 g/cm³
• Vapor Pressure: 9.42E-06mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: Keep Cold
• Solubility: soluble in Methanol
• PKA: 6.62±0.10(Predicted)
• BRN: 9119918
• CAS DataBase Reference: 2-Bromopyridine-5-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromopyridine-5-boronic acid(223463-14-7)
• EPA Substance Registry System: 2-Bromopyridine-5-boronic acid(223463-14-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• RIDADR: 2811
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 223463-14-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

Uses

Reactant involved in:Iterative cross-coupling reactions for synthesis of non-cytotoxic terpyridinesThe Garlanding approach for synthesis of phenyl-pyridyl scaffoldsCyanation for synthesis of aromatic nitrilesSuzuki-Miyaura cross-coupling with dihalopyridines and dihalobipyridinesPetasis boronic Mannich reaction

General Description

May contain varying amounts of anhydride

InChI:InChI=1/C5H5BBrNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 5419-55-6 Triisopropyl borate 
• 20511-12-0 2-amino-5-iodopyridine 
• 73290-22-9 2-bromo-5-iodo-pyridine 
• 504-29-0 2-aminopyridine 

Downstream Products

• 942189-65-3 2-(6-bromo-pyridin-3-yl)-pyrimidine 
• 942206-15-7 5,6'-dibromo-3,3'-bipyridine 
• 1115231-46-3 5'',6-dibromo-3,2':5',3''-terpyridine 
• 942206-04-4 6-bromo-6'-chloro-3,3'-bipyridine 
• 942206-17-9 6,6'-dibromo-2,3'-bipyridine 
• 1115231-45-2 6,6'-dibromo-3,2':6',3''-terpyridine 
• 942206-14-6 4,6'-dibromo-2,3'-bipyridine 
• 942206-16-8 6,2'-dibromo-3,4'-bipyridine 
• 1115231-48-5 5,6'-dibromo-[2,3']bipyridine 
• 342618-54-6 6'-bromo-[2,3']bipyridinyl 
• 1228271-66-6 4-[5-(4-Hexyloxy-phenyl)-pyridin-2-yl]-benzoic acid 
• 1228271-63-3 4-(6-(4-(hexyloxy)phenyl)pyridin-3-yl)benzoic acid 
• 1381889-73-1 C₂₀H₁₈BrNO₃ 
• 1400740-37-5 N-{2-[4-(6-bromo-pyridin-3-yl)-phenyl]-1-fluoromethyl-2-hydroxy-ethyl}-2,2-dichloro-acetamide 

Relevant articles and documents

ANTIMICROBIAL AGENTS

The present invention relates to the field of anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. More particularly, the invention relates to substituted aromatic compounds useful as therapeutic agents.

Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters

This paper describes a general method for the synthesis and isolation of novel 6-halo-pyridin-3-yl-boronic acids and esters 2-5. These compounds are prepared taking in account a regioselective halogen-metal exchange with a trialkylborate starting from 2,5-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 a range of arylhalides and authorise a strategy to produce new pyridines libraries.