22353-33-9

Basic information

• Product Name: 3-CHLORO-5-NITROPYRIDINE
• Synonyms: 3-CHLORO-5-NITROPYRIDINE;3-Chloro-5-nitropyridine97%;3-CHLORO-5-NITROPYRIDINE 97%
• CAS NO: 22353-33-9
• Molecular Formula: C₅H₃ClN₂O₂
• Molecular Weight: 158.54
• Product Categories: pharmacetical;Pyridine series;Pyridine;Pyridines;Heterocycle-Pyridine series
• Mol File: 22353-33-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 228.2°Cat760mmHg
• Flash Point: 91.8°C
• Appearance: /
• Density: 1.489g/cm³
• Vapor Pressure: 0.112mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-CHLORO-5-NITROPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-5-NITROPYRIDINE(22353-33-9)
• EPA Substance Registry System: 3-CHLORO-5-NITROPYRIDINE(22353-33-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 22353-33-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

InChI:InChI=1/C5H3ClN2O2/c6-4-1-5(8(9)10)3-7-2-4/h1-3H

Upstream product

• 626-60-8 3-Chloropyridine 
• 865186-94-3 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 22353-46-4 5-chloro-2-hydrazino-3-nitropyridine 
• 21427-62-3 2,5-dichloro-3-nitropyridine 

Downstream Products

• 1210868-16-8 3-(benzylsulfanyl)-5-chloropyridine 
• 3430-19-1 5-methylpyridin-3-amine 
• 6960-20-9 3-methyl-5-nitropyridine 

Relevant articles and documents

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

Preparation of nitropyridines by nitration of pyridines with nitric acid

Preparation of nitropyridines by nitration of pyridines with nitric acid was discussed. Trifluoroacetic anhydride was chilled in an ice bath and the pyridine or substituted pyridines were slowly added and stirred at chilled conditions for 2 h. Relative amounts of the reactants were required for the nitration of pyridine were characterized by 1H and Nuclear magnetic resonance (NMR) spectroscopy and elemental analysis. It was observed that the yields of β-nitropyridines obtained using the standard protocol were generally higher than those obtained using N2O3.