25412-53-7

Usage

Uses

Used in Organic Synthesis:
4-ACETAMIDOBENZYLAMINE is used as a precursor in the synthesis of various pharmaceuticals, playing a crucial role in the development of new drugs and therapeutic agents.
Used in Dye Production:
4-ACETAMIDOBENZYLAMINE is utilized in the production of dyes, contributing to the coloration and enhancement of various materials and products.
Used in Fine Chemicals Industry:
4-ACETAMIDOBENZYLAMINE serves as a building block in the synthesis of fine chemicals, which are essential in a wide range of applications, from cosmetics to agrochemicals.
Used in Heterocyclic Compound Synthesis:
As a key component in the synthesis of heterocyclic compounds, 4-ACETAMIDOBENZYLAMINE is instrumental in creating complex organic molecules with diverse applications in the pharmaceutical and chemical industries.
Used in Chemical Research:
4-ACETAMIDOBENZYLAMINE is employed as a reagent in chemical research, aiding scientists in understanding chemical reactions and developing new methodologies for organic synthesis.
Used in Medicinal Chemistry and Drug Discovery:
4-ACETAMIDOBENZYLAMINE holds potential applications in medicinal chemistry and drug discovery, making it a valuable asset in the search for new therapeutic agents and treatments.

InChI:InChI=1/C9H12N2O/c1-7(12)11-9-4-2-8(6-10)3-5-9/h2-5H,6,10H2,1H3,(H,11,12)

Upstream product

• 35704-19-9 N-(4-cyanophenyl)acetamide 
• 1253778-94-7 N-(4-((N-(phenylsulfonyl)phenylsulfonamido)methyl)phenyl)acetamide 
• 122-85-0 para-acetamidobenzaldehyde 
• 4403-71-8 (4-aminomethyl)aniline 
• 108-24-7 acetic anhydride 

Downstream Products

• 389601-56-3 N-(4-acetylamino-phenylmethyl)-3-(4'-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid amide 
• 1581755-38-5 (R)-N-(4-acetamidobenzyl)-1-(1-(naphthalen-1-yl)ethyl)-piperidine-4-carboxamide 
• 1061862-41-6 N-[4-(acetylamino)benzyl]-4-[(trifluoromethyl)thio]benzamide 
• 1027158-05-9 N-{4-[(7-chloro-6-nitro-quinazolin-4-ylamino)-methyl]-phenyl}-acetamide 

Relevant academic research and scientific papers

A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation

Cobalt-doped hybrid materials consisting of metal oxides and carbon derived from chitin were prepared, characterized and tested for industrially relevant nitrile hydrogenations. The optimal catalyst supported onto MgO showed, after pyrolysis at 700 °C, magnesium oxide nanocubes decorated with carbon-enveloped Co nanoparticles. This special structure allows for the selective hydrogenation of diverse and demanding nitriles to the corresponding primary amines under mild conditions (e.g. 70 °C, 20 bar H2). The advantage of this novel catalytic material is showcased for industrially important substrates, including adipodinitrile, picolinonitrile, and fatty acid nitriles. Notably, the developed system outperformed all other tested commercial catalysts, for example, Raney Nickel and even noble-metal-based systems in these transformations.

Ambient-Temperature Synthesis of Primary Amines via Reductive Amination of Carbonyl Compounds

Efficient synthesis of primary amines via low-temperature reductive amination of carbonyl compounds using NH3 and H2 as the nitrogen and hydrogen resources is highly desired and challenging in the chemistry community. Herein, we employed naturally occurring phytic acid as a renewable precursor to fabricate titanium phosphate (TiP)-supported Ru nanocatalysts with different reduction degrees of RuO2 (Ru/TiP-x, x represents the reduction temperature) by combining ball milling and molten-salt processes. Very interestingly, the obtained Ru/TiP-100 had good catalytic performance for the reductive amination of carbonyl compounds at ambient temperature, resulting from the synergistic cooperation of the support (TiP) and the Ru/RuO2 with a suitable proportion of Ru0 (52%). Various carbonyl compounds could be efficiently converted into the corresponding primary amines with high yields. More importantly, the conversion of other substrates with reducible groups could also be achieved at ambient temperature. Detailed investigations indicated that the partially reduced Ru and the support (TiP) were indispensable. The high activity and selectivity of Ru/TiP-100 catalyst originates from the relatively high acidity and the suitable electron density of metallic Ru0.

Liquid-phase hydrogenation of nitriles to amines facilitated by a co(ii)/zn(0) pair: a ligand-free catalytic protocol

The given report introduces a simple and user-friendly in situ method for the production of catalytically active cobalt particles. The approach circumvents the use of air-and moisture-sensitive reductants as well as the application of anhydrous Co-precursor salts. Accordingly, the described catalytic system is readily assembled under open-flask conditions by simply combining the components in the reaction vessel. Therefore, the arduous charging procedure of the reaction autoclave in a glovebox under an inert gas atmosphere is no longer necessary. In fact, the catalytically active material is obtained upon treatment of readily available Co(OAc)2·4 H2O with benign commercial Zn powder. The catalytic performance of the resultant material was tested in the heterogeneous hydrogenation of nitriles to the corresponding primary amines. Both activity and selectivity of the cobalt catalyst are significantly enhanced if a triflate-based Lewis acid and ammonia is added to the reaction mixture.

Metal-free remote oxidative benzylic C?H amination of 4-methylanilides with N-fluorobenzenesulfonimide

A metal-free remote oxidative benzylic C?H amination of 4-methylanilides with N-fluorobenzenesulfonimide was reported. The reaction was promoted by a hypervalent iodine reagent and can be handled under mild and neutral conditions, providing the highly regioselective benzylic C?H amination products even with multi-substituted 4-methylanilides. It provided a novel and facile method for the construction of C(sp3)–N bonds.

Selective Hydrogenation of Nitriles to Primary Amines by using a Cobalt Phosphine Catalyst

A general procedure for the catalytic hydrogenation of nitriles to primary amines by using a non-noble metal-based system is presented. Co(acac)3 in combination with tris[2-(dicyclohexylphosphino)ethyl]phosphine efficiently catalyzes the selective hydrogenation of a wide range of (hetero)aromatic and aliphatic nitriles to give the corresponding amines.

Graphene-Supported NiPd Alloy Nanoparticles for Effective Catalysis of Tandem Dehydrogenation of Ammonia Borane and Hydrogenation of Nitro/Nitrile Compounds

Monodisperse NiPd alloy nanoparticles (NPs) are synthesized and assembled on graphene (G) or other support to provide clean, efficient catalysis of tandem reactions—dehydrogenation of ammonia borane (AB) and hydrogenation of R—NO2 and/or R—CN to R—NH2. The tandem reactions proceed quickly and with high efficiency in aqueous methanol solutions at room temperature, and the supported catalyst is readily recovered for re-use, providing a simple, efficient and ‘green’ route to the preparation of many common pharmaceutical, dye or other chemical products. NiPd alloy NPs of 3.4 nanometer size were prepared by co-reduction of nickel(II) acetate and palladium(II) acetlyacetonate by borane-tert-butylamine in oleylamine and deposited on G via a solution phase self-assembly process. The G-NiPd showed composition-dependent catalysis on the tandem reaction with G-Ni30Pd70 being the most active. A variety of R—NO2 and/or R—CN derivatives (R alkyl or aryl) were reduced selectively into R—NH2 via G-Ni30Pd70 catalyzed tandem reaction in short (5-30 minute) reaction times with conversion yields reaching up to 100%, demonstrating a new approach to G-NiPd-catalyzed dehydrogenation of AB and hydrogenation of R—NO2 and R—CN. The G-NiPd NP catalyst is efficient and is reusable; thus the reaction can be performed in an environment-friendly process with short reaction times and high yields.

A Mild and Base-Free Protocol for the Ruthenium-Catalyzed Hydrogenation of Aliphatic and Aromatic Nitriles with Tridentate Phosphine Ligands

A novel protocol for the general hydrogenation of nitriles in the absence of basic additives is described. The system is based on the combination of [Ru(cod)(methylallyl)2] (cod=cyclooctadiene) and L2. A variety of aromatic and aliphatic nitriles is hydrogenated under mild conditions (50 °C and 15 bar H2) with this system. Kinetic studies revealed higher activity in the case of aromatic nitriles compared with aliphatic ones.

Tandem dehydrogenation of ammonia borane and hydrogenation of nitro/nitrile compounds catalyzed by graphene-supported NiPd alloy nanoparticles

We report a facile synthesis of monodisperse NiPd alloy nanoparticles (NPs) and their assembly on graphene (G) to catalyze the tandem dehydrogenation of ammonia borane (AB) and hydrogenation of R-NO2 and/or R-CN to R-NH2 in aqueous methanol solutions at room temperature. The 3.4 nm NiPd alloy NPs were prepared by coreduction of nickel(II) acetate and palladium(II) acetlyacetonate by borane-tert-butylamine in oleylamine and deposition on G via a solution phase self-assembly process. G-NiPd showed composition-dependent catalysis on the tandem reaction with G-Ni 30Pd70 being the most active. A variety of R-NO 2 and/or R-CN derivatives were reduced selectively into R-NH 2 via G-Ni30Pd70 catalyzed tandem reaction in 5-30 min reaction time with the conversion yields reaching up to 100%. Our study demonstrates a new approach to G-NiPd-catalyzed dehydrogenation of AB and hydrogenation of R-NO2 and R-CN. The G-NiPd NP catalyst is efficient and reusable, and the reaction can be performed in an environment-friendly process with short reaction times and high yields.

Selective catalytic transfer hydrogenation of nitriles to primary amines using Pd/C

The catalytic transfer hydrogenation of (hetero)aryl nitriles using ammonium formate has been investigated in detail. In the presence of commercially available Pd/C, a straightforward and selective reduction is achieved without any additives under mild conditions.

Nucleophilic Attack vs General Base Assisted Hydrolysis in the Reactions of Acetic Anhydride with Primary and Secondary Amines. pH-Yield Studies in the Recognition and Assessement of the Nucleophilic and General Base Reactions

The reaction of a set of primary and secondary amines with acetic anhydride in water at 25 deg C gave variable yields of the N-substituted acetamide in seven of the eight amines studied.The yield of the amide as a function of pH revealed the incursion in the most cases of a general base assisted hydrolysis of the acetic anhydride by the amine.From the pKa's of the amines and kw and kOH for acetic anhydride (the specific rates for the reaction of the anhydride with water and hydroxide, respectively), both kDN (for the formation of acetamides) and kGB (for the general base assisted hydrolysis) may be readily evaluated by fitting the pH-yield-data to pH-yield or pH-product ratio profiles.The reactions of ethyl chloroformate with aniline and benzylamine in water also showed the presence of the general base assisted reaction.It is concluded that (a) pH-yield data provide a new way of showing the existence of general base assisted hydrolysis in the presence of a direct nucleophilic displacement reaction, (b) the general base promoted reaction is sufficiently prevalent that it would be prudent to check specifically for its presence in any investigation of mechanisms of acyl transfer in water, and (c) until the extent of general base promoted hydrolysis can be predicted adequately, the possibility of such a reaction makes it difficult to predict yields of the products of the direct attack, and hence just how suitable a medium water may be for a particular preparative acyl transfer reaction.