4,4'-Dinitro-2,2'-bipyridine - 18511-72-3

4,4'-Dinitro-2,2'-bipyridine

Catalog Number: EVT-344649
CAS Number: 18511-72-3
Molecular Formula: C10H6N4O4
Molecular Weight: 246.18 g/mol
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Product Introduction

Description

The compound 4,4'-Dinitro-2,2'-bipyridine is a derivative of bipyridine, which is a class of compounds known for their unique chemical properties. Bipyridine derivatives have been extensively studied due to their redox activity and electrochromic capabilities, making them valuable in various scientific and technological applications. The research on these compounds has led to the development of multifunctional materials that exhibit interesting phenomena such as chromism, which is a property that allows materials to change color based on different stimuli1.

Applications in Various Fields

Analytical Chemistry

In the field of analytical chemistry, 4,4'-Dinitro-2,2'-bipyridine derivatives are used as key building blocks for creating responsive compounds and materials. Their solvatochromic and environment-responsive characteristics make them suitable for developing sensors that can detect changes in the medium, such as solvent polarity or the presence of specific analytes1.

Catalysis

The study of bipyridine-mediated tetraboration has revealed the potential of these compounds in catalysis, particularly in nitrogen fixation. The ability to activate and reduce dinitrogen using bipyridine derivatives could revolutionize the production of ammonia and other nitrogen-containing compounds, which are essential for agriculture and industry2.

Neuroscience

Although not directly related to 4,4'-Dinitro-2,2'-bipyridine, the study of 4-aminopyridine provides insight into the presynaptic mechanisms of bipyridine compounds. These derivatives can influence intracellular calcium concentrations and protein phosphorylation, which are critical processes in neurotransmitter release and synaptic function3. This suggests that bipyridine derivatives could have applications in neurological research and the development of drugs targeting synaptic transmission.

Properties

CAS Number

18511-72-3

Product Name

4,4'-Dinitro-2,2'-bipyridine

IUPAC Name

4-nitro-2-(4-nitropyridin-2-yl)pyridine

Molecular Formula

C10H6N4O4

Molecular Weight

246.18 g/mol

InChI

InChI=1S/C10H6N4O4/c15-13(16)7-1-3-11-9(5-7)10-6-8(14(17)18)2-4-12-10/h1-6H

InChI Key

ULRVNIRBWWMQJT-UHFFFAOYSA-N

SMILES

C1=CN=C(C=C1[N+](=O)[O-])C2=NC=CC(=C2)[N+](=O)[O-]

Canonical SMILES

C1=CN=C(C=C1[N+](=O)[O-])C2=NC=CC(=C2)[N+](=O)[O-]
Mechanism of Action

The mechanism of action of bipyridine derivatives, including 4,4'-Dinitro-2,2'-bipyridine, often involves redox reactions and electrochromic effects. These compounds can undergo reversible oxidation and reduction, which is a key feature in their application in electronic devices and sensors. For instance, the redox activity of these derivatives is exploited in the creation of compounds that respond to environmental changes, such as solvent composition or the presence of specific ions1. Additionally, the theoretical exploration of bipyridine-mediated reactions, as seen in the reduction of dinitrogen via tetraboration, demonstrates the potential of these compounds in catalyzing chemical transformations. The cleavage of bonds and activation of molecules like N2 through bipyridine derivatives could lead to new methods of chemical synthesis and energy production2.

Method of Synthesis or Extraction
4,4'-Dinitro-2,2'-bipyridine can be synthesized by various methods, including the reaction of 2,2'-bipyridine with nitric acid and sulfuric acid, the reaction of 2,2'-bipyridine with nitric acid and acetic anhydride, and the reaction of 2,2'-bipyridine with nitric acid and acetic acid. The efficiency and yield of each method vary depending on the reaction conditions. The reaction of 2,2'-bipyridine with nitric acid and sulfuric acid is the most commonly used method, and it yields 4,4'-Dinitro-2,2'-bipyridine with a purity of over 95%. However, this method produces a large amount of waste and is not environmentally friendly. The reaction of 2,2'-bipyridine with nitric acid and acetic anhydride is more efficient and produces less waste, but it requires a higher reaction temperature. The reaction of 2,2'-bipyridine with nitric acid and acetic acid is the least efficient method, and it yields 4,4'-Dinitro-2,2'-bipyridine with a purity of only 60%.
Chemical Structure and Biological Activity
4,4'-Dinitro-2,2'-bipyridine has a molecular formula of C10H6N4O4 and a molecular weight of 254.18 g/mol. It has a planar structure with two nitro groups and two pyridine rings. 4,4'-Dinitro-2,2'-bipyridine has been shown to have biological activity, including antimicrobial, antitumor, and anti-inflammatory effects. The mechanism of action of 4,4'-Dinitro-2,2'-bipyridine is not fully understood, but it is believed to involve the inhibition of enzymes and the disruption of cellular processes.
Biological Effects
4,4'-Dinitro-2,2'-bipyridine has been shown to have both therapeutic and toxic effects on cells. It has been found to inhibit the growth of cancer cells and reduce inflammation in animal models. However, it has also been shown to be toxic to cells at high concentrations and can cause DNA damage and cell death. The potential therapeutic and toxic effects of 4,4'-Dinitro-2,2'-bipyridine depend on the dose and duration of exposure.
Future Perspectives and Challenges
The use of 4,4'-Dinitro-2,2'-bipyridine in scientific research is limited by its toxicity and potential environmental impact. Future research should focus on developing safer and more environmentally friendly methods of synthesis or extraction. Additionally, more research is needed to fully understand the mechanism of action of 4,4'-Dinitro-2,2'-bipyridine and its potential therapeutic and toxic effects. The future application of 4,4'-Dinitro-2,2'-bipyridine in scientific research will depend on the development of safer and more effective methods of synthesis or extraction and a better understanding of its biological effects.

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