6083-47-2

Usage

Uses

Used in Pharmaceutical Industry:
4-(Dimethylamino)benzamide is used as a building block for the preparation of various pharmaceuticals due to its versatile chemical structure and reactivity, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(Dimethylamino)benzamide is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, to enhance crop protection and yield.
Used in Dye Industry:
4-(Dimethylamino)benzamide is employed as a key intermediate in the production of dyes, imparting color and stability to various materials, including textiles and plastics.
Used as a Reagent in Chemical Reactions:
4-(Dimethylamino)benzamide serves as a reagent in the formation of amide bonds, a crucial step in the synthesis of peptides, proteins, and other bioactive molecules, facilitating the development of novel compounds with specific properties and functions.
Safety Considerations:
4-(Dimethylamino)benzamide is considered potentially hazardous if ingested, inhaled, or comes into contact with skin and eyes, necessitating proper handling and safety measures during its use in various applications.

Upstream product

• 4755-50-4 4-(dimethylamino)benzoyl chloride 
• 2835-68-9 4-aminobenzamide 
• 2929-84-2 (E)-4-dimethylaminobenzaldehyde oxime 
• 7474-31-9 p-N,N-dimethylaminobenzoic anhydride 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 2929-84-2 4-dimethylaminobenzaldehyde oxime 
• 530-44-9 4-(Dimethylamino)benzophenone 
• 108-88-3 toluene 
• 616-38-6 carbonic acid dimethyl ester 
• 141814-27-9 2-(2-Methoxyethoxy)ethyl methyl carbonate 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 1703-46-4 N,N-dimethyl-4-hydroxymethylaniline 
• 201230-82-2 carbon monoxide 

Downstream Products

• 530-44-9 4-(Dimethylamino)benzophenone 
• 111860-92-5 2-(4-Dimethylamino-phenyl)-4-hydroxy-5-methyl-[1,3]oxazin-6-one 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 78823-56-0 methyl N-[4-(dimethylamino)phenyl]carbamate 
• 492-80-8 auramine O 
• 1703-46-4 N,N-dimethyl-4-hydroxymethylaniline 
• 840-57-3 2-(p-dimethylaminophenyl)benzoxazole 
• 1621584-43-7 N-(2-oxoindolin-6-ylcarbamoyl)-4-(dimethylamino)benzamide 
• 1621584-31-3 4-(dimethylamino)benzoyl isocyanate 
• 38359-26-1 N-methyl-p-aminobenzamide 
• 52379-48-3 4-(dimethylamino)-N-phenylbenzimidamide 

Relevant academic research and scientific papers

Process Development of the Copper(II)-Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co-Substrate

The access towards chiral nitriles remains crucial in the synthesis of several pharmaceuticals. One approach is based on metal-catalyzed dehydration of chiral aldoximes, which are generated from chiral pool-derived aldehydes as substrates, and the use of a cheap and readily available nitrile as co-substrate and water acceptor. Dehydration of N-acyl α-amino aldoximes such as N-Boc-l-prolinal oxime catalyzed by copper(II) acetate provides access to the corresponding N-acyl α-amino nitriles, which are substructures of the pharmaceuticals Vildagliptin and Saxagliptin. In this work, a detailed investigation of the formation of the amide as a by-product at higher substrate loadings is performed. The amide formation depends on the electronic properties of the nitrile co-substrate. We could identify an acceptor nitrile which completely suppressed amide formation at high substrate loadings of 0.5 m even when being used with only 2 equivalents. In detail, utilization of trichloroacetonitrile as such an acceptor nitrile enabled the synthesis of N-Boc-cyanopyrrolidine in a high yield of 92 % and with full retention of the absolute configuration.

Half-Sandwich Iridium Complexes Based on β-Ketoamino Ligands: Preparation, Structure, and Catalytic Activity in Amide Synthesis

A series of β-ketoamino-based N,O-chelate half-sandwich iridium complexes with the general formula [Cp*IrClL] have been prepared in good yields. These air-insensitive iridium complexes showed desirable catalytic activity in an amide preparation under mild conditions. A number of amides with diverse substituted groups were furnished in a one-pot reaction with good-to-excellent yields through an amidation reaction of NH2OH·HCl with aldehydes in the presence of these iridium(III) precursors. The excellent catalytic activity, mild reaction conditions, and broad substrate scope gave this type of iridium catalyst potential for use in industry. All of the obtained iridium complexes were well characterized by different spectroscopy techniques. The exact molecular structure of complex 3 has been confirmed by single-crystal X-ray analysis.

Half-Sandwich Iridium Complexes for the One-Pot Synthesis of Amides: Preparation, Structure, and Diverse Catalytic Activity

Several types of air-stable N,O-coordinate half-sandwich iridium complexes containing Schiff base ligands with the general formula [Cp*IrClL] were synthesized in good yields. These stable iridium complexes displayed a good catalytic efficiency in amide synthesis. A variety of amides with different substituents were obtained in a one-pot procedure with excellent yields and high selectivities through the amidation of aldehydes with NH2OHHCl and nitrile hydration under the catalysis of complexes 1-4. The excellent and diverse catalytic activity, mild conditions, broad substance scope, and environmentally friendly solvent make this system potentially applicable in industrial production. Half-sandwich iridium complexes 1-4 were characterized by NMR, elemental analysis, and IR techniques. Molecular structures of complexes 2 and 3 were confirmed by single-crystal X-ray analysis.

Transamidation for the Synthesis of Primary Amides at Room Temperature

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst

Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H2O to a wide variety of aliphatic and (hetero)aromatic nitriles in tBuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal-ligand cooperative binding of the nitrile.

(Ar-tpy)RuII(ACN)3: A Water-Soluble Catalyst for Aldehyde Amidation, Olefin Oxo-Scissoring, and Alkyne Oxygenation

The synthetic chemists always look for developing new catalysts, sustainable catalysis, and their applications in various organic transformations. Herein, we report a new class of water-soluble complexes, (Ar-tpy)RuII(ACN)3, utilizing designed terpyridines possessing electron-donating and -withdrawing aromatic residues for tuning the catalytic activity of the Ru(II) complex. These complexes displayed excellent catalytic activity for several oxidative organic transformations including late-stage C-H functionalization of aldehydes with NH2OR to valuable primary amides in nonconventional aqueous media with excellent yield. Its diverse catalytic power was established for direct oxo-scissoring of a wide range of alkenes to furnish aldehydes and/or ketones in high yield using a low catalyst loading in the water. Its smart catalytic activity under mild conditions was validated for dioxygenation of alkynes to highly demanding labile synthons, 1,2-diketones, and/or acids. This general and sustainable catalysis was successfully employed on sugar-based substrates to obtain the chiral amides, aldehydes, and labile 1,2-diketones. The catalyst is recovered and reused with a moderate turnover. The proposed mechanistic pathway is supported by isolation of the intermediates and their characterization. This multifaceted sustainable catalysis is a unique tool, especially for late-stage functionalization, to furnish the targeted compounds through frequently used amidation and oxygenation processes in the academia and industry.

Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines

Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.

Magnetic Nanoparticle-Supported Cu–NHC Complex as an Efficient and Recoverable Catalyst for Nitrile Hydration

Magnetic nanoparticles supported N-heterocyclic carbene–Cu complex was prepared and authenticated by FT-IR, SEM, EDX, VSM, powder-XRD. The catalytic activity of these magnetically retrievable NPs was investigated for hydration of nitriles as the simplest route for the synthesis of amides in an atom-economical manner. A wide range of nitriles containing various functional groups such as olefin, aldehyde, nitro, carboxylic acid was examined in this transformation to generate their corresponding amides in the aqueous medium. The immobilized catalyst was easily recovered using an external magnet and reused for six times without significant loss of its catalytic activity. Graphical Abstract: [Figure not available: see fulltext.].

A continuous-flow synthesis of primary amides from hydrolysis of nitriles using hydrogen peroxide as oxidant

A continuous-flow synthesis of primary amides from hydrolysis of nitriles using hydrogen peroxide as oxidant has been developed. Using this procedure, a variety of nitriles could be smoothly transformed into the desired primary amides in good to excellent yields. The mild reaction conditions and the flowing reaction system greatly improved the safety and make the reaction easy to scale up.

Investigation of Nitrile Hydration Chemistry by Two Transition Metal Hydroxide Complexes: Mn-OH and Ni-OH Nitrile Insertion Chemistry

Herein we describe the synthesis of a series of nickel complexes, including the formation of [(iPrPNHP)Ni(PMe3)][BPh4] (iPrPNHP = HN(CH2CH2(PiPr2))2). The ability of this phosphine complex to perform the 1,2-addition of H2O to produce the Ni-OH species [(iPrPNHP)NiOH][BPh4] has been investigated. The nucleophilicity of the hydroxide moiety of both [(iPrPNHP)NiOH][BPh4] and the previously reported (iPrPNHP)MnOH(CO)2 was investigated through the hydration of aryl and alkyl nitriles, leading to the formation of a number of metal carboxamide (RC(O)NH-) bonds. This reactivity generated complexes with the general structures of [(iPrPNHP)Ni(NHC(O)R)][BPh4] for nickel and (iPrPNHP)Mn(NHC(O)R)(CO)2 for manganese. Under catalytic conditions, the hydration of nitriles using nickel complexes yielded only a single turnover. However, (iPrPNHP)MnOH(CO)2 produced several turnovers, and the reaction conditions were probed for optimization.