What Is 2-Bromo-4-fluoro-N-methylaniline?

2-Bromo-4-fluoro-N-methylaniline is an aromatic amine derivative bearing three distinct substituents on the benzene ring: a bromine atom at the 2-position (ortho), a fluorine atom at the 4-position (para), and an N-methyl group on the amine nitrogen. Its molecular formula is C₇H₇BrFN with a molecular weight of approximately 204.04 g/mol.

The compound belongs to the class of halogenated N-alkylanilines and serves primarily as a versatile synthetic building block. The ortho-bromo substituent provides a handle for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Heck reactions, while the para-fluoro group can participate in nucleophilic aromatic substitution (SNAr) under appropriate conditions. The secondary amine (N–H absent; tertiary nitrogen is not present — the nitrogen bears one methyl and the aryl, making it a secondary amine) adds further functionalization potential.

This compound is of significant interest in medicinal chemistry as a pharmaceutical intermediate and in materials science for the synthesis of functional organic molecules.

Physicochemical Properties and Structure

The molecule exhibits a planar aromatic ring with electronic effects modulated by both the electron-withdrawing halogens (Br and F) and the electron-donating N-methyl amino group. The net electronic character of the ring is influenced by the interplay of these substituents, affecting regioselectivity in further functionalization reactions.

Key physicochemical characteristics include:

• Appearance: Typically a pale yellow to amber liquid or low-melting solid (verify with CoA).
• Molecular Weight: 204.04 g/mol
• Molecular Formula: C₇H₇BrFN
• Solubility: Expected to be soluble in common organic solvents such as dichloromethane, ethyl acetate, THF, and DMSO; limited aqueous solubility.
• Stability: Stable under normal storage conditions when kept away from strong oxidizers and moisture.

Researchers should consult the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) supplied by Aladdin Scientific for confirmed physical constants including melting/boiling point, density, and purity specification.

Synthetic Applications and Reactivity

2-Bromo-4-fluoro-N-methylaniline is valued in synthetic chemistry for its multifunctional reactivity:

1. Palladium-Catalyzed Cross-Coupling: The C–Br bond at the 2-position undergoes oxidative addition to Pd(0) complexes, enabling Suzuki–Miyaura coupling with boronic acids/esters, Buchwald–Hartwig amination, and Heck reactions to introduce aryl, alkenyl, or amine groups.
2. Nucleophilic Aromatic Substitution (SNAr): The para-fluorine, activated by the adjacent electron-withdrawing environment, can be displaced by nucleophiles such as amines, alkoxides, and thiolates under appropriate conditions.
3. N-Functionalization: The secondary amine nitrogen can be acylated, alkylated, or used in reductive amination sequences to produce tertiary amines or amides, enabling access to a wide range of N-substituted derivatives.
4. Pharmaceutical Intermediate: The compound is employed as a key building block in the synthesis of biologically active molecules, including kinase inhibitors and other drug candidates where the halogenated aniline motif is a common pharmacophore.

When planning reactions, chemists should consider the steric influence of the ortho-bromo group on reaction rates and selectivity.

Safe Handling, Storage, and Regulatory Notes

As with all halogenated aromatic amines, 2-Bromo-4-fluoro-N-methylaniline should be handled with appropriate caution:

• Personal Protective Equipment (PPE): Wear chemical-resistant gloves, laboratory coat, and safety goggles. Use in a well-ventilated fume hood to avoid inhalation of vapors or aerosols.
• Storage: Store in tightly sealed containers in a cool (typically 2–8 °C or room temperature per CoA), dry, and well-ventilated area, away from direct light, heat sources, strong oxidizing agents, and strong acids or bases.
• Disposal: Dispose of waste in accordance with local, regional, and national regulations for halogenated organic compounds. Do not pour down the drain.
• SDS: Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before handling. The SDS contains GHS classification, first-aid measures, fire-fighting procedures, and spill-handling guidance specific to this compound.

Aromatic amines as a class may present health hazards; refer to the SDS for the specific hazard classification of this compound. Regulatory status may vary by jurisdiction — procurement teams should verify import/export requirements as applicable.

Ordering and Quality Information from Aladdin Scientific

Aladdin Scientific supplies 2-Bromo-4-fluoro-N-methylaniline under SKU B733256. Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity (typically by NMR and/or GC-MS), purity, and physical appearance.

To order or obtain further product information:

• Visit the Aladdin Scientific website and search by SKU B733256 or the product name.
• Contact your regional Aladdin Scientific representative or customer service team for bulk pricing, custom quantities, or expedited delivery inquiries.
• Request the SDS and CoA through the product page or by contacting customer support directly.

For quality questions, lot-specific data requests, or technical application support, Aladdin Scientific's technical team is available to assist research and procurement professionals.