2-Bromo-5-methoxy-4-methylaniline: Properties & Lab Use Guide

2-Bromo-5-methoxy-4-methylaniline is a multifunctional halogenated aromatic amine building block widely used in pharmaceutical synthesis, agrochemical research, and fine-chemical development owing to its reactive bromo substituent, nucleophilic amino group, and electron-donating methoxy and methyl substituents.

Chemical Name

2-Bromo-5-methoxy-4-methylaniline

SKU

B193787

Molecular Formula

C8H10BrNO

Molecular Weight

216.08 g/mol

Key Functional Groups

Primary amine (–NH2), aryl bromide (C–Br), methoxy (–OCH3), methyl (–CH3)

Recommended Storage

Cool, dry, well-ventilated location; protect from light and moisture

Primary Applications

Pharmaceutical intermediates, cross-coupling reactions, diazonium chemistry

Chemical Identity and Structure

2-Bromo-5-methoxy-4-methylaniline (SKU B193787) is an ortho-bromoaniline derivative bearing three distinct substituents on the benzene ring: a primary amino group (–NH2) at position 1, a bromine atom at position 2, an electron-donating methoxy group (–OCH3) at position 5, and a methyl group (–CH3) at position 4. Its molecular formula is C₈H₁₀BrNO with a molecular weight of approximately 216.08 g/mol.

The combination of an electron-donating amino group and a methoxy group renders the ring electron-rich at specific positions, while the bromine at the ortho position relative to the amine provides a versatile handle for metal-catalyzed cross-coupling reactions. The methyl substituent further modulates steric and electronic properties, making this compound a valuable and differentiated building block compared with simpler bromoaniline analogs.

Synthetic Applications and Reactivity

The two principal reactive sites of 2-Bromo-5-methoxy-4-methylaniline — the aryl bromide and the primary amine — can be exploited independently or sequentially, offering considerable synthetic versatility:

• Palladium-catalyzed cross-coupling: The C–Br bond participates readily in Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira reactions, enabling the introduction of aryl, heteroaryl, vinyl, or alkynyl groups. These transformations are commonly used to assemble biaryl or heteroaromatic cores found in drug candidates.
• Diazotization and diazonium chemistry: The primary amine can be converted to a diazonium salt under standard conditions (NaNO2, HCl, 0–5 °C), which can then undergo Sandmeyer reactions, azo coupling, or nucleophilic substitution, broadening the range of accessible analogs.
• Acylation and sulfonylation: The –NH2 group reacts with acyl chlorides, anhydrides, or sulfonyl chlorides to yield amides and sulfonamides, which are privileged motifs in medicinal chemistry.
• Heterocycle synthesis: Bifunctional anilines of this type serve as precursors to benzimidazoles, indoles, quinolines, and related nitrogen-containing heterocycles through condensation reactions.

Researchers designing multi-step synthetic routes should consider the relative reactivity of the amine versus the aryl bromide under specific reaction conditions to ensure chemoselectivity.

Handling, Safety, and Storage Guidelines

As with all aromatic amine compounds, appropriate precautions must be observed when handling 2-Bromo-5-methoxy-4-methylaniline:

• Personal protective equipment (PPE): Wear chemically resistant gloves (e.g., nitrile), a laboratory coat, and safety goggles. Where dust or aerosol generation is possible, use a fume hood or respiratory protection.
• Skin and eye contact: Aromatic amines can be absorbed through the skin. Wash affected areas immediately and thoroughly with soap and water. In case of eye contact, rinse with copious water for at least 15 minutes and seek medical attention.
• Storage: Store in a tightly sealed container in a cool (2–8 °C recommended), dry, and well-ventilated location, away from oxidizing agents, strong acids, and sources of ignition. Protect from light and moisture to prevent decomposition or discoloration.
• Disposal: Dispose of in accordance with local, regional, and national regulations governing halogenated organic waste. Do not pour down drains.

Always consult the current Safety Data Sheet (SDS) for B193787 before use. The SDS contains up-to-date hazard classifications, first-aid measures, and regulatory information.

Quality, Purity, and Specification Considerations

For reliable experimental outcomes, the purity and quality of 2-Bromo-5-methoxy-4-methylaniline are critical parameters. Researchers and procurement teams should consider the following when selecting a lot:

• Purity assessment: Typical analytical methods include HPLC (area normalization), GC, and NMR spectroscopy (1H and 13C). A purity of ≥97% by HPLC is generally considered suitable for synthetic applications; confirm the certificate of analysis (CoA) for the specific lot.
• Appearance: The compound is typically a solid or crystalline powder. Significant discoloration (deep brown or black) may indicate oxidative degradation of the amine and should prompt re-evaluation before use.
• Structural confirmation: Mass spectrometry or NMR data confirming the molecular ion and key fragment patterns is the gold standard for identity verification.
• Moisture content: Karl Fischer titration may be advisable for moisture-sensitive downstream applications.

Contact Aladdin Scientific for the CoA, SDS, and additional technical documentation for SKU B193787. Custom purity grades or pack sizes may be available upon request.

Frequently asked questions

What are the main synthetic uses of 2-Bromo-5-methoxy-4-methylaniline?

This compound serves primarily as a bifunctional building block in medicinal chemistry and fine-chemical synthesis. The aryl C–Br bond is exploited in palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig, Sonogashira), while the primary amine undergoes acylation, sulfonylation, diazotization, and heterocycle-forming condensations. Together these reactivities allow efficient construction of complex drug-like scaffolds.

How should 2-Bromo-5-methoxy-4-methylaniline be stored to maintain stability?

Store the compound in a tightly sealed container at 2–8 °C in a cool, dry, and well-ventilated area away from light, moisture, oxidizing agents, and strong acids. Aromatic amines are susceptible to oxidative discoloration over time; proper storage minimizes degradation and preserves reagent quality for longer periods.

Is 2-Bromo-5-methoxy-4-methylaniline suitable for Suzuki–Miyaura cross-coupling reactions?

Yes, the aryl bromide functionality in this compound is well-suited for Suzuki–Miyaura cross-coupling with aryl or heteroaryl boronic acids under palladium catalysis. The electron-donating amino and methoxy groups influence ring electronics and may affect reaction rates; optimization of catalyst system, base, solvent, and temperature is recommended for best yields.

What safety precautions are required when handling this compound?

Use nitrile gloves, a laboratory coat, and safety goggles at all times. Conduct all weighing and transfer operations inside a fume hood to avoid inhalation of dust or vapors. Aromatic amines can be absorbed dermally; wash any skin contact immediately with soap and water. Consult the Safety Data Sheet (SDS) for SKU B193787 for full hazard and first-aid information before use.

How can I verify the purity and identity of the received batch?

Request the Certificate of Analysis (CoA) for your specific lot from Aladdin Scientific, which typically reports HPLC purity, melting point, and NMR data. For independent verification, 1H NMR, 13C NMR, and high-resolution mass spectrometry (HRMS) are the recommended techniques to confirm structural identity, while HPLC provides a quantitative purity assessment.

References

1. March, J.; Smith, M. B. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed.; Wiley: Hoboken, NJ, 2013. (General reference for aromatic amine and aryl halide reactivity.)
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
3. Hartwig, J. F. Palladium-Catalyzed Amination of Aryl Halides and Related Reactions. Acc. Chem. Res. 1998, 31, 852–860. doi:10.1021/ar970188v
4. Aladdin Scientific. Certificate of Analysis, SKU B193787, 2-Bromo-5-methoxy-4-methylaniline. (Internal document; available on request.)

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