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2-Methyl-5-nitronicotinic acid
[CAS# 59290-81-2]

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Identification
ClassificationPharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Nitropyridine
Name2-Methyl-5-nitronicotinic acid
Molecular StructureCAS # 59290-81-2, 2-Methyl-5-nitronicotinic acid
Molecular FormulaC7H6N2O4
Molecular Weight182.13
CAS Registry Number59290-81-2
EC Number868-221-2
SMILESCC1=C(C=C(C=N1)[N+](=O)[O-])C(=O)O
Safety Data
Hazard Symbolssymbol   GHS07 Warning  Details
Risk StatementsH302-H315-H319-H335  Details
Safety StatementsP261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.4H302
Specific target organ toxicity - single exposureSTOT SE3H335
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2AH319
SDSAvailable
up Discovery and Applications
2-Methyl-5-nitronicotinic acid is an organic compound belonging to the class of nitro-substituted pyridines. This compound, with the molecular formula C7H6N2O4, features a pyridine ring substituted with a methyl group at the second position and a nitro group at the fifth position. The presence of both a carboxylic acid group and a nitro group on the aromatic ring gives 2-Methyl-5-nitronicotinic acid unique chemical properties, making it a valuable intermediate in various fields of organic synthesis, pharmaceuticals, and materials science.

The discovery of 2-Methyl-5-nitronicotinic acid is part of the broader study of nicotinic acid derivatives, which have been of interest to chemists due to their biological significance and versatile reactivity. Nicotinic acid, also known as niacin or vitamin B3, is a vital nutrient involved in numerous metabolic processes. By modifying its structure through the introduction of functional groups such as methyl and nitro, researchers have been able to explore a wide range of chemical and biological activities.

One of the primary applications of 2-Methyl-5-nitronicotinic acid is in organic synthesis, where it serves as a building block for the construction of more complex molecules. The nitro group on the pyridine ring is a strong electron-withdrawing group, which makes the ring more susceptible to nucleophilic substitution reactions. This property allows 2-Methyl-5-nitronicotinic acid to be used in the synthesis of heterocyclic compounds, which are commonly found in pharmaceuticals and agrochemicals. The methyl group, on the other hand, can participate in various reactions, including oxidative processes and cross-coupling reactions, further expanding the utility of this compound in synthetic chemistry.

In the pharmaceutical industry, derivatives of 2-Methyl-5-nitronicotinic acid are explored for their potential therapeutic applications. The nitro group can be reduced to form amino derivatives, which are often biologically active and can interact with enzymes or receptors in the body. These derivatives are studied for their potential as anti-inflammatory, antimicrobial, and anticancer agents. The pyridine ring itself is a common scaffold in drug design, and the ability to modify its substituents through reactions involving 2-Methyl-5-nitronicotinic acid makes this compound an important intermediate in medicinal chemistry.

Moreover, 2-Methyl-5-nitronicotinic acid is used in the development of materials, particularly in the creation of coordination complexes with metals. The carboxylic acid group can coordinate with metal ions to form stable complexes, which are of interest in areas such as catalysis, electronic materials, and metal-organic frameworks (MOFs). These metal complexes can exhibit unique properties, such as enhanced catalytic activity or specific electronic characteristics, making them useful in various industrial applications.

Additionally, 2-Methyl-5-nitronicotinic acid finds application in the field of analytical chemistry. Its ability to form colored complexes with certain metal ions makes it a useful reagent for detecting and quantifying these ions in various samples. This application is particularly valuable in environmental monitoring and quality control processes, where precise measurement of metal ion concentrations is essential.

In summary, 2-Methyl-5-nitronicotinic acid is a versatile compound with significant applications in organic synthesis, pharmaceuticals, materials science, and analytical chemistry. Its discovery and subsequent development as a derivative of nicotinic acid have opened up new possibilities for the design of complex molecules and advanced materials, underscoring its importance in both scientific research and industrial processes.

References

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