Chemical Identity and Structure

N-Acetyl 3,5-dibromoaniline, also named N-(3,5-dibromophenyl)acetamide, is an aromatic acetamide featuring a phenyl ring symmetrically substituted with bromine atoms at the 3- and 5-positions and an acetamido group (–NHCOCH₃) at the 1-position. Its molecular formula is C₈H₇Br₂NO with a molecular weight of approximately 292.95 g/mol. The symmetric placement of the two bromine substituents imparts useful electronic and steric properties, rendering the compound particularly valuable as a building block in multi-step organic synthesis.

The acetamido protecting group moderates the reactivity of the aniline nitrogen, reducing its nucleophilicity and directing electrophilic aromatic substitution reactions to predictable ring positions. This combination of features—aryl bromide handles for cross-coupling and a masked amine—makes N-Acetyl 3,5-dibromoaniline an efficient bifunctional synthon.

Synthetic Applications and Reactivity

The two aryl C–Br bonds in N-Acetyl 3,5-dibromoaniline are well-suited for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings. These reactions allow researchers to introduce diverse aryl, heteroaryl, alkynyl, or amino substituents at the 3- and/or 5-positions, rapidly generating structural diversity from a single scaffold.

The acetamide group can be hydrolyzed under acidic or basic aqueous conditions to regenerate the free aniline, providing access to 3,5-dibromoaniline derivatives after further functionalization. Alternatively, the acetamide nitrogen can be alkylated or acylated to produce N,N-disubstituted variants. The compound is therefore a strategic precursor in the preparation of biologically active molecules, dyes, and specialty polymers that require a symmetrically halogenated aniline core.

In agrochemical and pharmaceutical discovery programs, symmetrically brominated anilines such as this compound serve as key intermediates for herbicide, fungicide, and kinase-inhibitor scaffolds, though researchers should consult primary literature for specific structural analogs.

Handling, Storage, and Safety

As with all organobromine compounds containing an aniline moiety, N-Acetyl 3,5-dibromoaniline should be handled with appropriate precautions. Researchers are advised to work in a well-ventilated fume hood and wear appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a lab coat, to minimize dermal and inhalation exposure.

The compound should be stored in a tightly sealed container, away from strong oxidizing agents, strong bases, and sources of ignition. Cool, dry storage conditions (typically room temperature to slightly below, in a desiccated environment) help maintain long-term purity and stability. Consult the product's Safety Data Sheet (SDS) for jurisdiction-specific disposal, transport classification, and first-aid procedures before use.

Waste containing brominated aromatic compounds must be disposed of in accordance with local environmental regulations; do not pour down the drain or discard with general laboratory waste.

Specification and Quality Considerations

When sourcing N-Acetyl 3,5-dibromoaniline for research use, purity is a critical parameter. Impurities such as the mono-brominated analogue (N-acetyl 3-bromoaniline or N-acetyl 5-bromoaniline) or unreacted starting aniline can interfere with downstream reactions, particularly sensitive cross-coupling protocols where the catalyst loading is low.

Aladdin Scientific supplies this compound under SKU N180016. Researchers should request or review the Certificate of Analysis (CoA) for each lot, checking purity by HPLC or GC, and verifying the identity by melting point, NMR, or mass spectrometry data as appropriate for their application. Lot-to-lot consistency is especially important in structure–activity relationship (SAR) studies.

For procurement enquiries, volume pricing, or custom purity grades, contact Aladdin Scientific's technical support team to discuss your project requirements.