Overview and Structural Features

4-Bromo-3,5-dichloroaniline is a halogenated aromatic primary amine featuring a benzene ring substituted with a bromine atom at the para position (C-4) and chlorine atoms at both meta positions (C-3 and C-5) relative to the amino group. This symmetric trihalogen substitution pattern renders the aromatic ring strongly electron-deficient, moderately reducing the nucleophilicity of the amine while simultaneously activating the ring toward nucleophilic aromatic substitution and providing multiple handles for transition-metal-catalyzed cross-coupling chemistry.

The compound is catalogued under Aladdin Scientific SKU B727671 and is offered as a research-grade reagent for laboratory use. Its well-defined substitution pattern makes it a valuable building block for the controlled introduction of halogen diversity in target molecules.

Physicochemical Properties and Stability

As a trihalogenated aniline derivative, 4-Bromo-3,5-dichloroaniline is expected to be a relatively stable solid at ambient temperature. The electron-withdrawing halogens lower the basicity of the amine compared to unsubstituted aniline, which is itself a weak base (pKa ~4.6 in water). Reactivity toward electrophilic aromatic substitution is reduced, while susceptibility to nucleophilic aromatic substitution and oxidative coupling is increased relative to electron-rich anilines.

The compound should be stored in a cool, dry place away from light, moisture, and incompatible materials such as strong oxidizers, strong acids, and reactive acyl halides. Sealed container storage under an inert atmosphere (nitrogen or argon) is recommended for long-term stability. Like all aromatic amines, it should be handled with appropriate personal protective equipment (PPE) and in a well-ventilated fume hood.

Synthetic Applications and Reactivity

4-Bromo-3,5-dichloroaniline is a multifunctional building block exploited across several reaction classes:

• Palladium-catalyzed cross-coupling: The C–Br bond, being more reactive than C–Cl bonds toward oxidative addition to Pd(0), serves as the preferred site for Suzuki–Miyaura, Heck, Buchwald–Hartwig, and related reactions, enabling selective functionalization while leaving the C–Cl bonds intact for further elaboration.
• Diazonium chemistry: The primary amine can be diazotized under standard conditions (NaNO₂/HCl, 0–5 °C) to give the diazonium salt, which can undergo Sandmeyer reactions, azo coupling, or Balz–Schiemann fluorination.
• Amide and sulfonamide formation: The amine group reacts with acyl chlorides, acid anhydrides, or sulfonyl chlorides to give pharmaceutically relevant amide and sulfonamide derivatives.
• Nucleophilic aromatic substitution (SNAr): The combined electron-withdrawing effect of three halogens activates the ring toward SNAr with nucleophiles such as alkoxides, thiolates, and amines.

These diverse reaction pathways make the compound particularly attractive in the early-stage synthesis of active pharmaceutical ingredients (APIs), agrochemical intermediates, and functional organic materials.

Safe Handling, Storage, and Disposal

Handling: Aromatic amines as a chemical class carry potential toxicological concerns. Personnel should wear nitrile gloves, safety glasses, and a lab coat as minimum PPE. Work should be performed in a certified chemical fume hood. Avoid inhalation of dust or vapors, and avoid skin and eye contact.

Storage: Store in a tightly closed container in a cool (typically 2–8 °C or room temperature per SDS), dry, well-ventilated area away from incompatible substances (strong oxidizers, strong acids). Protect from light to minimize photodegradation.

Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing halogenated organic waste. Do not pour down the drain. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for full hazard classification and first-aid measures before use.

Note: Users must consult the current SDS for B727671 prior to use. Specific GHS hazard classifications and first-aid procedures are detailed therein.

Ordering Information and Product Availability

4-Bromo-3,5-dichloroaniline is available from Aladdin Scientific under SKU B727671. Researchers and procurement teams can obtain current pricing, available pack sizes, purity specifications, and stock status directly through the Aladdin Scientific website or by contacting customer service. Bulk quantities and custom packaging may be available upon request.

For questions regarding specifications, certificates of analysis (CoA), or Safety Data Sheets (SDS), please contact Aladdin Scientific technical support or your regional sales representative.