2-Methyl-3-nitroaniline: Properties, Safety & Lab Use Guide

2-Methyl-3-nitroaniline is an aromatic amine building block bearing both an amino group and an ortho-nitro substituent on a toluene scaffold, making it a versatile intermediate in organic synthesis, dye chemistry, and pharmaceutical research.

IUPAC Name

2-methyl-3-nitroaniline

CAS Number

603-83-8

Molecular Formula

C₇H₈N₂O₂

Molecular Weight

152.15 g/mol

Appearance

Orange to dark-orange crystalline solid

Primary Use

Organic synthesis intermediate; dye and pharmaceutical building block

Aladdin SKU

M106751

Physicochemical Properties

2-Methyl-3-nitroaniline (CAS 603-83-8) has the molecular formula C₇H₈N₂O₂ and a molecular weight of approximately 152.15 g/mol. The compound features a benzene ring substituted with an amino group (–NH₂) at position 1, a methyl group (–CH₃) at position 2, and a nitro group (–NO₂) at position 3. This arrangement creates intramolecular steric and electronic interactions that influence its reactivity profile.

The compound is typically obtained as an orange to dark-orange crystalline solid at room temperature. Its melting point is reported in the range of 92–96 °C, and it exhibits limited solubility in water but dissolves well in common organic solvents such as ethanol, acetone, dichloromethane, and dimethyl sulfoxide (DMSO). The presence of both electron-donating (–NH₂) and electron-withdrawing (–NO₂) groups on the ring provides a basis for selective electrophilic and nucleophilic transformations.

Applications in Organic Synthesis and Research

2-Methyl-3-nitroaniline serves as a versatile building block in multiple areas of chemical research and industrial chemistry:

• Dye and Pigment Synthesis: Nitroanilines are classical precursors in azo dye manufacturing. The free amino group of 2-Methyl-3-nitroaniline can be diazotized and coupled with appropriate coupling agents to generate azo colorants used in textile and analytical applications.
• Pharmaceutical Intermediates: The compound is used as a starting material or intermediate for the preparation of heterocyclic compounds, including benzimidazoles, quinoxalines, and related scaffolds with potential biological activity.
• Cross-Coupling and Functionalization: The amine functionality enables derivatization via acylation, sulfonylation, and reductive chemistry, while the nitro group can be reduced to yield the corresponding 1,2,3-trisubstituted phenylenediamine for further condensation reactions.
• Material Science Research: Substituted nitroanilines have been investigated as components of nonlinear optical (NLO) materials and charge-transfer complexes due to their push-pull electronic character.

Safe Handling, Storage, and Disposal

Hazard Overview: Like many aromatic amines and nitro compounds, 2-Methyl-3-nitroaniline should be treated as a potential health hazard. Aromatic amines as a chemical class are associated with toxic and potentially mutagenic properties. Users should consult the current Safety Data Sheet (SDS) before handling.

Personal Protective Equipment (PPE): Always wear appropriate chemical-resistant gloves (e.g., nitrile), a laboratory coat, and safety goggles when handling this compound. Work in a well-ventilated fume hood to avoid inhalation of dust or vapors.

Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location, away from oxidizing agents, strong acids, and sources of heat or ignition. Recommended storage temperature is typically 2–8 °C or as specified on the product label. Protect from light to prevent photodegradation.

Disposal: Dispose of waste material in accordance with applicable local, regional, and national regulations governing hazardous chemical waste. Do not dispose of down drains or in municipal waste streams without appropriate treatment.

Quality, Purity, and Ordering Information

Aladdin Scientific offers 2-Methyl-3-nitroaniline (SKU: M106751) as a research-grade reagent. For optimal experimental reproducibility, verify purity specifications—typically assessed by methods such as HPLC or GC—prior to use in sensitive synthetic or analytical workflows.

When selecting a lot, review the Certificate of Analysis (CoA) for recorded melting point, purity percentage, and any reported impurities. Batch-to-batch consistency is especially important when the compound is used as a reference standard or as a critical intermediate in multi-step syntheses.

For bulk quantities, custom purity grades, or specific packaging requirements, contact Aladdin Scientific's technical sales team. Procurement teams can request quotes and review lead times through the Aladdin online platform.

Frequently asked questions

What is 2-Methyl-3-nitroaniline used for in the laboratory?

2-Methyl-3-nitroaniline is primarily used as a building block in organic synthesis. Key applications include the preparation of azo dyes via diazotization, the synthesis of pharmaceutical intermediates such as benzimidazoles and quinoxalines, and research into nonlinear optical materials. The nitro group can also be selectively reduced to expand the range of accessible derivatives.

How should 2-Methyl-3-nitroaniline be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, protected from light and away from oxidizing agents and strong acids. A recommended storage temperature of 2–8 °C is typical; always refer to the product label and current SDS for lot-specific guidance.

What safety precautions are required when handling 2-Methyl-3-nitroaniline?

Users must wear chemical-resistant gloves (nitrile recommended), a laboratory coat, and safety goggles. All handling should be performed inside a ventilated fume hood to prevent inhalation of dust or vapors. Consult the Safety Data Sheet (SDS) for complete hazard information before use, and dispose of waste according to local hazardous chemical regulations.

What is the molecular formula and molecular weight of 2-Methyl-3-nitroaniline?

2-Methyl-3-nitroaniline has the molecular formula C₇H₈N₂O₂ and a molecular weight of approximately 152.15 g/mol.

Where can I find the Certificate of Analysis (CoA) for Aladdin's 2-Methyl-3-nitroaniline?

The Certificate of Analysis for 2-Methyl-3-nitroaniline (SKU: M106751) can be accessed through the Aladdin Scientific website by searching the product SKU or CAS number. You may also contact Aladdin's customer service team to request lot-specific documentation directly.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for aromatic amine reactivity and nitro compound chemistry.
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. Reference for diazotization and azo coupling reactions of aromatic amines.
3. Aladdin Scientific. Product Page: 2-Methyl-3-nitroaniline, SKU M106751. Aladdin Scientific website.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.