2124-31-4

Usage

Chemical Properties

off-white crystalline powder

Uses

4''-Dimethylaminoacetophenone

InChI:InChI=1/C10H13NO/c1-8(12)9-4-6-10(7-5-9)11(2)3/h4-7H,1-3H3

Upstream product

• 880142-29-0 trans-α-bromo-4-dimethylamino-cinnamic acid 
• 108-24-7 acetic anhydride 
• 121-69-7 N,N-dimethyl-aniline 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 917-64-6 methyl magnesium iodide 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 50-00-0 formaldehyd 
• 99-92-3 p-aminobenzophenone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 64-19-7 acetic acid 
• 79-16-3 N-methyl-acetamide 
• 463-51-4 Ketene 
• 127-19-5 N,N-dimethyl acetamide 

Downstream Products

• 100723-07-7 4-[(4-dimethylamino-phenyl)-oxo-thioacetyl]-morpholine 
• 100722-58-5 4-[(4-dimethylamino-phenyl)-thioxo-thioacetyl]-morpholine 
• 1681-94-3 4-dimethylaminochalcone 
• 105905-95-1 (4-dimethylamino-phenyl)-thioacetic acid dimethylamide 
• 121167-59-7 1-(4-dimethylamino-phenyl)-ethanone-phenylhydrazone 
• 126443-08-1 (E)-1,3-bis(4-(dimethylamino)phenyl)prop-2-en-1-one 
• 111241-31-7 3-ethyl-2-[2-(4-dimethylamino-phenyl)-propenyl]-benzothiazolium; iodide 
• 111528-52-0 2-[2-(4-dimethylamino-phenyl)-propenyl]-3-methyl-benzothiazolium; iodide 
• 113062-19-4 2-(4-dimethylamino-phenyl)-3-(4-methoxy-phenyl)-butane-2,3-diol 
• 4150-37-2 N,N-dimethyl-4-ethylaniline 
• 54441-61-1 ethyl 3-(4-(dimethylamino)phenyl)-3-oxopropanoate 

Relevant academic research and scientific papers

Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol

Methanol is a potential hydrogen source and C1 synthon, which finds interesting applications in both chemical synthesis and energy technologies. The effective utilization of this simple alcohol in organic synthesis is of central importance and attracts scientific interest. Herein, we report a clean and cost-competitive method with the use of methanol as both C1 synthon and H2 source for selective N-methylation of amines by employing relatively cheap RuCl3.xH2O as a ligand-free catalyst. This readily available catalyst tolerates various amines comprising electron-deficient and electron-donating groups and allows them to transform into corresponding N-methylated products in moderate to excellent yields. In addition, few marketed pharmaceutical agents (e. g., venlafaxine and imipramine) were also successfully synthesized via late-stage functionalization from readily available feedstock chemicals, highlighting synthetic value of this advanced N-methylation reaction. Using this platform, we also attempted tandem reactions with selected nitroarenes to convert them into corresponding N-methylated amines using MeOH under H2-free conditions including transfer hydrogenation of nitroarenes-to-anilines and prepared drug molecules (e. g., benzocaine and butamben) as well as key pharmaceutical intermediates. We further enable one-shot selective and green syntheses of 1-methylbenzimidazole using ortho-phenylenediamine (OPDA) and methanol as coupling partners.

Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki–Miyaura-Coupling and Transfer-Hydrogenation Cascade

We report a means to achieve the addition of two disparate nucleophiles to the amide carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki–Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing stereogenic centers via cascade processes.

NHC ligand-based half-sandwich iridium complexes: synthesis, structure and catalytic activity in acceptorless dehydrogenation and transfer hydrogenation

A set of neutral C,C-chelate half-sandwich iridium(iii) complexes have been prepared with NHC ligands that contain pendant aromatic rings as potentially chelating donor sites. The catalytic activity of such iridium complexes has been investigated for the acceptorless dehydrogenation (AD) reactions of alcohols and for the transfer hydrogenation reactions of ketones. The prepared iridium(iii) complexes show excellent catalytic activity for AD reactions of a wide range of secondary alcohols, and they are also shown to be effective for the synthesis of aldehydes from primary alcohols without the observation of undesired byproducts such as esters. Additionally, these complexes are also highly efficient in transfer hydrogenation of ketones and aldehydes, which give the alcohols in good yields under mild conditions. The exact structure and bonding mode of the NHC-based iridium complexes was identified using various spectroscopic methods and single crystal X-ray analysis.

Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism

Ruthenium-catalyzed oxidative dehydrogenation of alcohols using carbodiimide as an efficient hydrogen acceptor has been developed. The protocol exhibits wide substrate scope with good to excellent yields. The results of the kinetic analysis indicated that the reaction mechanism includes the hydrogen transfer process and that the addition of carbodiimide is essential for the reaction system, and the resulting amidine also could react as a hydrogen acceptor.

Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides

A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.

Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains

Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents.

Preparation method of aromatic ketone

The invention discloses a preparation method of aromatic ketone. Under the effects of a palladium catalyst and a nitrogen-containing ligand, nitrile compounds and arylsulfonylhydrazide take desulfurization addition reaction in an organic solvent; after the reaction is completed, post treatment is performed to obtain aromatic ketone. The reaction is applicable to aromatic nitrile compounds, and isalso applicable to aliphatic nitrile compounds; the reaction realizes the wide substrate applicability and functional group tolerance; the potential application value is realized in the aspect of aryl-carbonyl building.

Pd(II)-Catalyzed Denitrogenative and Desulfinative Addition of Arylsulfonyl Hydrazides with Nitriles

A Pd(II)-catalyzed denitrogenative and desulfinative addition of arylsulfonyl hydrazides with nitriles has been successfully achieved under mild conditions. This transformation is a new method for the addition reaction to nitriles with arylsulfonyl hydrazides as arylating agent, thus providing an alternative synthesis of aryl ketones. The reported addition reaction is tolerant to many common functional groups, and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported denitrogenative and desulfinative addition was also appropriate for alkyl nitriles, making this newly developed transformation attractive.

Tropylium Ion Catalyzes Hydration Reactions of Alkynes

The hydration of alkynes is one of the most atom-economic and versatile synthetic protocols to access carbonyl compounds. This fundamental reaction, however, often requires transition-metal catalysts or harsh reaction conditions to promote the addition of water to the carbon–carbon triple bond. In this work, it is demonstrated that the non-benzenoid aromatic tropylium ion can be used as an organic Lewis acid promoter for the hydration of alkynes under simple reaction conditions with excellent outcomes.

Efficient and Selective N-Methylation of Nitroarenes under Mild Reaction Conditions

Herein, we report a straightforward protocol for the preparation of N,N-dimethylated amines from readily available nitro starting materials using formic acid as a renewable C1 source and silanes as reducing agents. This tandem process is efficiently accomplished in the presence of a cubane-type Mo3PtS4 catalyst. For the preparation of the novel [Mo3Pt(PPh3)S4Cl3(dmen)3]+ (3+) (dmen: N,N′-dimethylethylenediamine) compound we have followed a [3+1] building block strategy starting from the trinuclear [Mo3S4Cl3(dmen)3]+ (1+) and Pt(PPh3)4 (2) complexes. The heterobimetallic 3+ cation preserves the main structural features of its 1+ cluster precursor. Interestingly, this catalytic protocol operates at room temperature with high chemoselectivity when the 3+ catalyst co-exists with its trinuclear 1+ precursor. N-heterocyclic arenes, double bonds, ketones, cyanides and ester functional groups are well retained after N-methylation of the corresponding functionalized nitroarenes. In addition, benzylic-type as well as aliphatic nitro compounds can also be methylated following this protocol.