951677-39-7

Basic information

• Product Name: 2,3-dichloro-4-pyridineboronic acid
• Synonyms: 4-Borono-2,3-dichloropyridine;2,3-Dichloropyridine-4-boronic Acid (contains varying amounts of Anhydride);2,3-Dichloropyridine-4-boronic acid;2,3-Dichloro-4-pyridineboronic acid
• CAS NO: 951677-39-7
• Molecular Formula: C₅H₄BCl₂NO₂
• Molecular Weight: 191.81
• Product Categories: blocks;BoronicAcids;Pyridines;Boronic acid;Organoborons;Pyridine;alkyl chloride|boric acid
• Mol File: 951677-39-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 136-138°C
• Boiling Point: 375.683 °C at 760 mmHg
• Flash Point: 181.007 °C
• Appearance: /
• Density: 1.567 g/cm³
• Vapor Pressure: 2.6E-06mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Soluble in organic solvents.
• PKA: 6.27±0.58(Predicted)
• CAS DataBase Reference: 2,3-dichloro-4-pyridineboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dichloro-4-pyridineboronic acid(951677-39-7)
• EPA Substance Registry System: 2,3-dichloro-4-pyridineboronic acid(951677-39-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 951677-39-7(Hazardous Substances Data)

Usage

Description

2,3-dichloro-4-pyridineboronic acid is an organic compound that features a pyridine ring with two chlorine atoms at the 2nd and 3rd positions and a boronic acid group at the 4th position. This chemical structure endows it with unique properties that make it a versatile building block in organic synthesis and a valuable reagent in various analytical techniques.

Uses

Used in HPLC and NMR Chromatography:
2,3-dichloro-4-pyridineboronic acid is used as a chromatographic reagent for the separation and analysis of complex mixtures in high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. Its unique chemical properties allow for selective interactions with target compounds, improving the resolution and sensitivity of these analytical methods.
Used in Cross-Coupling Reactions:
2,3-dichloro-4-pyridineboronic acid is used as a synthetic intermediate in various cross-coupling reactions, which are essential for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis. Its boronic acid functionality enables it to participate in palladium-catalyzed reactions, such as Suzuki-Miyaura, Heck, and Sonogashira couplings, facilitating the construction of diverse molecular architectures and the synthesis of complex organic compounds.

InChI:InChI=1/C5H4BCl2NO2/c7-4-3(6(10)11)1-2-9-5(4)8/h1-2,10-11H

Upstream product

• 2402-77-9 2,3-dichloro-pyridine 

Downstream Products

• 1073353-78-2 2,3-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 

Relevant articles and documents

(Dimethoxy- and dihalopyridyl)boronic acids and highly functionalized heteroarylpyridines by Suzuki cross-coupling reactions

We report the synthesis of (2,6-dimethoxy-3-pyridyl)boronic acid (2), (2,3-dimethoxy-4-pyridyl)boronic acid (4), (2,6-difluoro-3-pyridyl)boronic acid (6), (2,6-dichloro-3-pyridyl)-boronic acid (8) and (2,3-dichloro-4-pyridyl) boronic acid (10) by directed ortho-metalation reactions on the corresponding disubstituted pyridine precursor, followed by the reaction with triisopropyl borate (TPB) or trimethyl borate. The reactivity of the pyridylboronic acids with heteroaryl halides in Suzuki-Miyaura cross-coupling reactions has been evaluated. New highly functionalized heteroarylpyridine derivatives have thereby been obtained in moderate to high yields. The reaction of 8 and 3-amino-2-chloropyridine yielded the rare 5H-pyrrolo[2,3-b:4,5-b′] dipyridine (i.e. 1,5-diazacarbazole) ring system by sequential cross-coupling and intramolecular cyclisation reactions. The X-ray crystal structures are reported for the pyridylboronic acids 2, 4, 8 and 10. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.