588-07-8

Usage

Uses

Used in Agricultural Industry:
3'-Chloroacetanilide is used as a metabolite in the agricultural industry for its role in the degradation and breakdown of chlorpropham, an acetanilide herbicide. This process contributes to the overall effectiveness and safety of the herbicide in controlling weed growth while minimizing potential environmental impact.
Used in Chemical Research and Development:
In the field of chemical research and development, 3'-chloroacetanilide is utilized as a key compound for studying the properties and behavior of acetanilide herbicide derivatives. This helps in the development of new and improved herbicides with enhanced efficacy and reduced environmental impact.
Used in Environmental Monitoring:
3'-Chloroacetanilide is also used in environmental monitoring as a marker for the presence and degradation of chlorpropham in the environment. This aids in assessing the effectiveness of the herbicide and its potential impact on ecosystems, allowing for better management and mitigation strategies.

Upstream product

• 108-24-7 acetic anhydride 
• 108-42-9 3-chloro-aniline 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 5177-66-2 1-ethoxyvinyl acetate 
• 89415-71-4 3-Chlor-2-cyclohexen-1-onoxim 
• 128915-30-0 N-(3-Chloro-phenyl)-N'-(4-nitro-phenyl)-acetamidine 
• 91731-86-1 C₁₄H₁₁Cl₂N₃O 
• 29551-86-8 N-chloro-m-chloroacetanilide 
• 121-44-8 triethylamine 
• 2754-27-0 trimethylsilyl acetate 
• 75813-68-2 Butyl-(3-chloro-phenyl)-amine 
• 546-67-8 lead(IV) tetraacetate 
• 64-17-5 ethanol 

Downstream Products

• 2150-93-8 N-(3,4-dichlorophenyl)acetamide 
• 101-17-7 3-chlorodiphenylamine 
• 105836-67-7 (2-chloro-phenyl)-(3-chloro-phenyl)-amine 
• 107058-34-4 N-(3-chloro-phenyl)-N-(2-methoxy-phenyl)-acetamide 
• 103273-72-9 acetic acid-(4-acetyl-3-chloro-anilide) 
• 90798-26-8 acetic acid-(3-chloro-4-chloroacetyl-anilide) 
• 302926-88-1 bis-(3-acetylamino-phenyl)-ether 
• 10416-62-3 Trimethylsilylderivat von m-Chloracetanilid 
• 25946-91-2 (3-chloro-phenyl)-(3,4-dimethoxy-phenyl)-amine 
• 5833-26-1 Acetyl-(3-chloro-phenyl)-carbamic acid isopropyl ester 
• 63243-77-6 2-acetylamino-4-chlorobenzoic acid ethyl ester 
• 102677-68-9 N-(3-Acetylamino-5-chloro-benzyl)-2-chloro-acetamide 
• 15258-44-3 N-ethyl-3-chloroaniline 
• 712-33-4 3-chloro-4-nitroacetanilide 

Relevant academic research and scientific papers

One-Pot Regioselective and Stereoselective Synthesis of C-Glycosyl Amides from Glycals Using Vinyl Azides as Glycosyl Acceptors

The reaction of glycals containing good leaving groups with aromatic vinyl azides to give α-C-glycosyl amides in good yields is described. Various vinyl azides with different groups undergo the reaction smoothly. In these reactions, an iminodiazonium intermediate is generated by the attack of the vinyl azide onto the glycal under Lewis acid conditions. This undergoes Schmidt-type denitrogenative 1,2-migration to form a nitrilium ion, which, upon hydrolysis, gives the desired C-glycosyl amide.

Design, synthesis, kinetic, molecular dynamics, and hypoglycemic effect characterization of new and potential selective benzimidazole derivatives as Protein Tyrosine Phosphatase 1B inhibitors

Protein-tyrosine phosphatase 1B (PTP1B) is a negative regulator of insulin signaling pathway and has been validated as a therapeutic target for type 2 diabetes. A wide variety of scaffolds have been included in the structure of PTP1B inhibitors, one of them is the benzimidazole nucleus. Here, we report the design and synthesis of a new series of di- and tri- substituted benzimidazole derivatives including their kinetic and structural characterization as PTP1B inhibitors and hypoglycemic activity. Results show that compounds 43, 44, 45, and 46 are complete mixed type inhibitors with a Ki of 12.6 μM for the most potent (46). SAR type analysis indicates that a chloro substituent at position 6(5), a β-naphthyloxy at position 5(6), and a p-benzoic acid attached to the linker 2-thioacetamido at position 2 of the benzimidazole nucleus, was the best combination for PTP1B inhibition and hypoglycemic activity. In addition, molecular dynamics studies suggest that these compounds could be potential selective inhibitors from other PTPs such as its closest homologous TCPTP, SHP-1, SHP-2 and CDC25B. Therefore, the compounds reported here are good hits that provide structural, kinetic, and biological information that can be used to develop novel and selective PTP1B inhibitors based on benzimidazole scaffold.

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Hybrid quinoline-thiosemicarbazone therapeutics as a new treatment opportunity for Alzheimer’s disease-synthesis, in vitro cholinesterase inhibitory potential and computational modeling analysis

Alzheimer’s disease (AD) is a progressive neurodegenerative disorder and the leading cause of dementia worldwide. The limited pharmacological approaches based on cholinesterase inhibitors only provide symptomatic relief to AD patients. Moreover, the adverse side effects such as nausea, vomiting, loss of appetite, muscle cramps, and headaches associated with these drugs and numerous clinical trial failures present substantial limitations on the use of medications and call for a detailed insight of disease heterogeneity and development of preventive and multifactorial therapeutic strategies on urgent basis. In this context, we herein report a series of quinoline-thiosemicarbazone hybrid therapeutics as selective and potent inhibitors of cholinesterases. A facile multistep synthetic approach was utilized to generate target structures bearing multiple sites for chemical modifications and establishing drug-receptor interactions. The structures of all the synthesized compounds were fully established using readily available spectroscopic techniques (FTIR, 1H- and 13C-NMR). In vitro inhibitory results revealed compound 5b as a promising and lead inhibitor with an IC50 value of 0.12 ± 0.02 μM, a 5-fold higher potency than standard drug (galantamine; IC50 = 0.62 ± 0.01 μM). The synergistic effect of electron-rich (methoxy) group and ethylmorpholine moiety in quinolinethiosemicarbazone conjugates contributes significantly in improving the inhibition level. Molecular docking analysis revealed various vital interactions of potent compounds with amino acid residues and reinforced the in vitro results. Kinetics experiments revealed the competitive mode of inhibition while ADME properties favored the translation of identified inhibitors into safe and promising drug candidates for pre-clinical testing. Collectively, inhibitory activity data and results from key physicochemical properties merit further research to ensure the design and development of safe and high-quality drug candidates for Alzheimer’s disease.

Cu(OTf)2-Mediated Cross-Coupling of Nitriles and N-Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products**

Metal-catalyzed C–N cross-coupling generally forms C?N bonds by reductive elimination from metal complexes bearing covalent C- and N-ligands. We have identified a Cu-mediated C–N cross-coupling that uses a dative N-ligand in the bond-forming event, which, in contrast to conventional methods, generates reactive cationic products. Mechanistic studies suggest the process operates via transmetalation of an aryl organoboron to a CuII complex bearing neutral N-ligands, such as nitriles or N-heterocycles. Subsequent generation of a putative CuIII complex enables the oxidative C–N coupling to take place, delivering nitrilium intermediates and pyridinium products. The reaction is general for a range of N(sp) and N(sp2) precursors and can be applied to drug synthesis and late-stage N-arylation, and the limitations in the methodology are mechanistically evidenced.

Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds

We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.

Aryne Precursors for Selective Generation of 3-Haloarynes: Preparation and Application to Synthetic Reactions

The synthesis and reaction of new 3-haloaryne precursors 2a-2h were studied. The ortho-(trimethylsilyl)aryl triflate precursors 2a-2h were prepared by a simple procedure involving O-trimethylsilylation and migration of a trimethylsilyl group followed by triflation. The remarkable feature of new precursors is the selective generation of 3-haloarynes by suppressing the competitive thia-Fries rearrangement, which is the problem in the reaction using the well-known 3-haloaryne precursors. The advantage of new precursor 2a over a typical precursor 1 was confirmed by the direct comparisons in several reactions. The application of precursors 2a-2h to the syntheses of heterocycles was also reported.