2-(3-methyl-6-nitro-3H-imidazo[4,5-b]pyridin-2-yl)ethan-1-amine | CAS 1784267-01-1

PRODUCT OVERVIEW

2-(3-methyl-6-nitro-3H-imidazo[4,5-b]pyridin-2-yl)ethan-1-amine | CAS 1784267-01-1  is a structurally sophisticated heterocyclic amine compound belonging to the imidazo[4,5-b]pyridine class. This class of fused bicyclic nitrogen-containing heterocycles is widely recognized in modern chemical and pharmaceutical research for its versatility and biological relevance. The compound integrates a methyl-substituted imidazo-pyridine core with a nitro functional group and a terminal primary amine, making it a valuable research intermediate and synthetic building block.

Due to its unique electronic and structural features, this molecule is primarily utilized in medicinal chemistry programs, heterocyclic synthesis, and structure–activity relationship (SAR) studies. Its well-defined scaffold enables chemists to design and modify downstream derivatives with precision, supporting exploratory research across multiple scientific disciplines.

CHEMICAL IDENTITY

• Chemical Name: 2-(3-methyl-6-nitro-3H-imidazo[4,5-b]pyridin-2-yl)ethan-1-amine

• CAS Number: 1784267-01-1

• Molecular Formula: C₉H₁₁N₅O₂

• Molecular Weight: 221.22 g/mol

• Compound Type: Nitro-substituted heterocyclic amine

• Core Structure: Imidazo[4,5-b]pyridine scaffold

The molecular architecture reflects a balance between aromatic rigidity and functional flexibility, offering multiple reactive sites suitable for synthetic derivatization and molecular optimization.

PHYSICOCHEMICAL CHARACTERISTICS

This compound exhibits physicochemical properties consistent with heterocyclic nitro amines of comparable complexity. The presence of multiple nitrogen atoms contributes to polar character and hydrogen-bonding capacity, while the aromatic fused ring system supports molecular stability and planarity. The predicted density and boiling point reflect strong intermolecular interactions arising from the nitro group and primary amine functionality.

Such properties are advantageous for laboratory-scale synthesis, analytical characterization, and incorporation into advanced molecular frameworks during drug discovery research.

STRUCTURAL AND FUNCTIONAL FEATURES

Imidazo[4,5-b]pyridine Core

The imidazo[4,5-b]pyridine scaffold is considered a privileged heterocycle in medicinal chemistry. Its fused aromatic system enables strong π-π stacking interactions and facilitates binding to diverse biological targets. This scaffold is frequently explored in the development of kinase inhibitors, enzyme modulators, and receptor-targeting compounds.

Methyl Substitution

The methyl group at the 3-position subtly influences lipophilicity and steric profile, allowing researchers to fine-tune molecular interactions and optimize pharmacokinetic behavior in derivative compounds.

Nitro Functional Group

The nitro substituent at the 6-position serves both as an electron-withdrawing group and a synthetic handle. It can modulate electronic distribution across the heterocycle and may be chemically transformed into other functional groups, such as amines, to expand chemical diversity.

Ethan-1-amine Side Chain

The terminal primary amine is a highly valuable functional group in synthetic chemistry. It supports a wide range of transformations, including amide coupling, urea formation, reductive amination, and salt formation, making this compound especially useful as an intermediate in multistep synthesis.

SYNTHETIC AND MEDICINAL CHEMISTRY APPLICATIONS

2-(3-methyl-6-nitro-3H-imidazo[4,5-b]pyridin-2-yl)ethan-1-amine is well suited for use as:

• A synthetic intermediate in heterocyclic compound development

• A building block for medicinal chemistry optimization

• A scaffold for SAR exploration

• A component of screening libraries for early-stage drug discovery

The compound’s multifunctional nature allows chemists to explore diverse chemical space while maintaining a stable and well-characterized core structure. It is particularly useful in projects where nitrogen-rich heterocycles are required to enhance target engagement or molecular specificity.

RESEARCH USE AND SCOPE

This compound is intended strictly for research and laboratory use. Typical areas of application include:

• Pharmaceutical and medicinal chemistry research

• Heterocyclic compound synthesis

• Lead optimization and molecular modification studies

• Academic and industrial R&D programs

It is not intended for human or veterinary use, clinical applications, or diagnostic purposes.

SUMMARY

2-(3-methyl-6-nitro-3H-imidazo[4,5-b]pyridin-2-yl)ethan-1-amine | CAS 1784267-01-1  is a high-value research compound offering a rare combination of a privileged heterocyclic core, a reactive primary amine, and a functional nitro group. Its structural versatility and synthetic utility make it an excellent choice for advanced research applications in medicinal chemistry and chemical biology. ResolveMass Laboratories Inc. supplies this compound to support innovation, precision synthesis, and cutting-edge scientific exploration.