N-Methyl-3,5-dinitro-2-pyridinamine | CAS 19404-40-1

PRODUCT OVERVIEW

N-Methyl-3,5-dinitro-2-pyridinamine
CAS: 19404-40-1
Molecular Formula: C6H6N4O4
Molecular Weight: 198.14 g/mol

N-Methyl-3,5-dinitro-2-pyridinamine | CAS 19404-40-1 is a functionalized pyridine derivative characterized by two strongly electron-withdrawing nitro groups at the 3- and 5-positions, and an N-methylated amino substituent at the 2-position of the pyridine ring. This combination of structural features renders the molecule of interest in specialized chemical synthesis, materials research, and advanced energetic formulation research.

The presence of nitro groups contributes to the compound’s high electron deficiency, polarizability, and potential energetic behavior, while the methylated aminopyridine core imparts unique coordination potential with metal centers and reactivity in nucleophilic substitution pathways. Such attributes make it a useful intermediate or research target in chemical innovation domains.

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CHEMICAL AND PHYSICAL PROPERTIES

The compound’s crystalline structure and high nitro content suggest dense molecular packing and significant inter- and intra-molecular interactions, which contribute to its thermal and electronic behavior.

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SYNTHETIC ROUTES AND CHEMICAL BEHAVIOR

N-Methyl-3,5-dinitro-2-pyridinamine is typically synthesized by nitration of an appropriate aminopyridine precursor followed by controlled N-methylation, although alternative methodologies and catalysts can be explored depending on scale and selectivity requirements.

Key Synthetic Considerations

• Precursor Selection: Starting from 2-aminopyridine derivatives enables regioselective nitration at the 3- and 5-positions under controlled conditions using nitrating agents such as nitric acid or nitric acid-based mixtures.

• Protecting Group Strategies: In some sequences, protecting groups on the amine help reduce side reactions and improve yield before subsequent methylation.

• N-Methylation: Can be achieved via classical reductive methylation (formaldehyde + reducing agent) or using methyl halides under basic conditions, with careful control of stoichiometry to avoid over-alkylation.

• Purification: Advanced chromatographic techniques and recrystallization from suitable organic solvents are used to isolate high-purity product.

Reactivity pathways of this compound are driven by the electron-deficient heterocycle, which makes it susceptible to nucleophilic aromatic substitution (SNAr) under certain conditions and capable of forming coordination complexes with transition metals. Its nitro substituents also make it of interest in studies of charge distribution and redox behavior.

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APPLICATIONS AND FUNCTIONAL USES

While not a common commodity chemical, N-Methyl-3,5-dinitro-2-pyridinamine | CAS 19404-40-1  is valuable in a range of advanced and specialized applications:

Specialty Chemical Synthesis

• Serves as a building block for heterocyclic compounds in medicinal chemistry and agrochemical research.

• Useful in designing electron-poor ligand scaffolds for organometallic chemistry.

• Precursor in exploratory pathways toward new functional materials.

Energetic Materials Research

• The highly nitrated structure exhibits properties of interest in energetic compound research, including density, heat of formation, and detonation parameters.

• Used in fundamental studies of how nitro group placement affects energetic performance.

Materials Science and Coordination Chemistry

• The pyridinamine backbone allows coordination to metals, enabling exploration of new complexes with magnetic, catalytic, or electronic properties.

• May be applied in research on conductive polymers or supramolecular assemblies.

Analytical Reference Standard

• Employed as a reference compound in high-performance liquid chromatography (HPLC), NMR, and mass spectrometry method development for structural elucidation of nitro-pyridine derivatives.

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REGULATORY AND COMPLIANCE NOTES

This compound is a research chemical and intermediate used in controlled laboratory environments. Users should consult relevant local, national, and international regulations regarding handling, transport, and disposal of nitroaromatic chemicals. Material Safety Data Sheets (MSDS) and institutional guidelines must be observed.