For organic chemists and R&D scientists, understanding the specific reactivity of chemical intermediates is key to designing efficient synthetic pathways. 2-Benzoyl-4-bromoaniline (CAS 39859-36-4) offers a unique combination of functional groups that make it particularly valuable for advanced synthetic transformations, especially in cross-coupling reactions.

The chemical structure of 2-Benzoyl-4-bromoaniline features a benzophenone core with an amino group at the ortho position and a bromine atom at the para position relative to the amino group. The bromine substituent is electron-withdrawing, which influences the electronic properties of the aromatic ring. Crucially, this aryl bromide moiety is highly susceptible to palladium-catalyzed cross-coupling reactions, a cornerstone of modern organic synthesis. These reactions enable the formation of new carbon-carbon or carbon-heteroatom bonds, allowing for the construction of complex molecular architectures.

One of the most significant applications of the bromine atom in 2-Benzoyl-4-bromoaniline is in Suzuki-Miyaura coupling. This reaction involves the palladium-catalyzed coupling of an aryl halide (in this case, the aryl bromide) with an aryl or vinyl boronic acid or ester. For example, reacting 2-Benzoyl-4-bromoaniline with an appropriate aryl boronic acid in the presence of a palladium catalyst, such as Pd(PPh3)4, and a base in a solvent mixture like THF/water, typically at elevated temperatures (e.g., 80°C), can efficiently introduce a new aryl group at the bromine-substituted position. This is a powerful method for building biaryl systems, which are common in many pharmaceuticals and advanced materials.

Another important cross-coupling reaction where this intermediate can be utilized is the Buchwald-Hartwig amination. This reaction allows for the formation of carbon-nitrogen bonds by coupling an aryl halide with an amine. While 2-Benzoyl-4-bromoaniline already possesses an amino group, the bromine atom can be used to attach other amine-containing fragments, further diversifying the molecular structure.

Chemists should be mindful of potential competing reactions. The presence of the amino group can sometimes interfere with certain palladium-catalyzed reactions. In such cases, protecting the amino group, for example, with a Boc (tert-butoxycarbonyl) anhydride, before performing the cross-coupling reaction can enhance selectivity and yield. The protecting group can then be removed under acidic conditions, such as with trifluoroacetic acid (TFA), to regenerate the free amine.

For researchers and procurement specialists looking to buy 2-Benzoyl-4-bromoaniline (CAS 39859-36-4) for their cross-coupling projects, sourcing from a reputable manufacturer is critical. Ensuring high purity and consistent reactivity is paramount. Our company, as a leading supplier of fine chemicals, provides 2-Benzoyl-4-bromoaniline with guaranteed specifications, supporting your advanced synthetic endeavors. We encourage you to inquire about pricing and availability for this versatile intermediate.

In conclusion, the bromine substituent on 2-Benzoyl-4-bromoaniline significantly enhances its utility in modern organic synthesis, particularly in palladium-catalyzed cross-coupling reactions. This makes it an indispensable intermediate for chemists aiming to construct complex molecules efficiently and effectively.