2150-93-8

Usage

Uses

Used in Pharmaceutical Industry:
3,4-DICHLOROACETANILIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a valuable building block for the development of new drugs with potential therapeutic applications.
Used in the Preparation of Triazolecarboxylic Acid Derivatives:
3,4-DICHLOROACETANILIDE is used as a starting material for the preparation of Triazolecarboxylic Acid derivatives. These derivatives have been identified as potential Glycolate Oxidase inhibitors, which can play a crucial role in the treatment of various diseases and conditions related to the overproduction or abnormal functioning of Glycolate Oxidase.

InChI:InChI=1/C8H7Cl2NO/c1-5(12)11-6-2-3-7(9)8(10)4-6/h2-4H,1H3,(H,11,12)

Upstream product

• 128-09-6 N-chloro-succinimide 
• 588-07-8 3-Chloroacetanilide 
• 75-36-5 acetyl chloride 
• 95-76-1 m,p-dichloroaniline 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 29551-86-8 N-chloro-m-chloroacetanilide 
• 7732-18-5 water 
• 64-19-7 acetic acid 
• 99-54-7 3,4-dichloronitrobenzene 
• 201230-82-2 carbon monoxide 
• 108-24-7 acetic anhydride 
• 139752-39-9 1-(3,4-dichlorophenyl)ethanone oxime 
• 405-02-7 1,2-dichloro-4-diazoniumbenzene tetrafluoroborate 

Downstream Products

• 5462-30-6 N-(4,5-dichloro-2-nitrophenyl)acetamide 
• 23627-24-9 N-(2,4,5-trichlorophenyl)acetamide 
• 99310-47-1 acetic acid-(2,3,4-trichloro-anilide) 
• 15862-03-0 4,5-Dichlor-N-nitroso-acetanilid 
• 123846-84-4 3-pyridine 
• 17847-40-4 N-ethyl-3,4-dichloroaniline 
• 6641-64-1 4,5-dichloro-2-nitroaniline 
• 958804-40-5 3,4-dichloro-2-nitro-aniline 
• 170806-27-6 4,5-dichloro-2-nitrophenylazide 
• 4701-01-3 5,6-dichlorobenzofuroxan 
• 634-67-3 2,3,4-trichloroaniline 
• 40157-48-0 2-nitro-3,4,6-trichloroaniline 
• 609818-66-8 N-(2-nitro-3,4,6-trichlorophenyl)-acetamide 
• 636-30-6 2,4,5-trichloroaniline 

Relevant academic research and scientific papers

Biotransformation of phenylurea herbicides by a soil bacterial strain, Arthrobacter sp. N2: Structure, ecotoxicity and fate of diuron metabolite with soil fungi

In order to assess the influence of the aromatic substitution on the ability of a soil bacterial strain, Arthrobacter sp. N2, to degrade phenylurea herbicides, biotransformation assays were performed in mineral medium with resting cells of this soil bacterial strain on three phenylurea herbicides (diuron, chlorotoluron and isoproturon). Each herbicide considered, led to the formation of only one metabolite detected by HPLC analysis. After isolation, the metabolites were identified by NMR and MS, as the corresponding substituted anilines. According to the Microtox test (realized on the bacterium Vibrio fischeri), these metabolites presented non-target toxicity far more important (up to 600 times higher for 4-isopropylaniline) than the parent molecule. For isoproturon and chlorotoluron, the amount of substituted anilines obtained at the end of the biotransformation was very low, whereas the biotransformation of diuron into 3,4-dichloroaniline was almost quantitative. In this last case, the degradation product accumulated in the medium. In soil, other microorganisms are present that might degrade it. So the biotransformation of 3,4-dichloroaniline was then tested with four fungal strains: Aspergillus niger, Beauveria bassiana, Cunninghamella echinulata var. elegans and Mortierella isabellina. The aniline was further transformed with all the microorganisms tested. Only one metabolite was detected by HPLC analysis and after isolation, it was identified to be 3,4-dichloroacetanilide. This acetylated compound led to biological effects less important on V. fischeri than 3,4-dichloroaniline. These results stress the importance of identifying the degradation products to assess the impact of a polluting agent. Indeed, the pollutant may undergo transformation yielding compounds more toxic than the parent molecule.

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.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.

N-acetylation of amines in continuous-flow with acetonitrile—no need for hazardous and toxic carboxylic acid derivatives

A continuous-flow acetylation reaction was developed, applying cheap and safe reagent, acetonitrile as acetylation agent and alumina as catalyst. The method developed utilizes milder reagent than those used conventionally. The reaction was tested on various aromatic and aliphatic amines with good conversion. The catalyst showed excellent reusability and a scale-up was also carried out. Furthermore, a drug substance (paracetamol) was also synthesized with good conversion and yield.

Transition-Metal-Free C-C, C-O, and C-N Cross-Couplings Enabled by Light

Transition-metal-catalyzed cross-couplings to construct C-C, C-O, and C-N bonds have revolutionized chemical science. Despite great achievements, these metal catalysts also raise certain issues including their high cost, requirement of specialized ligands, sensitivity to air and moisture, and so-called "transition-metal-residue issue". Complementary strategy, which does not rely on the well-established oxidative addition, transmetalation, and reductive elimination mechanistic paradigm, would potentially eliminate all of these metal-related issues. Herein, we show that aryl triflates can be coupled with potassium aryl trifluoroborates, aliphatic alcohols, and nitriles without the assistance of metal catalysts empowered by photoenergy. Control experiments reveal that among all common aryl electrophiles only aryl triflates are competent in these couplings whereas aryl iodides and bromides cannot serve as the coupling partners. DFT calculation reveals that once converted to the aryl radical cation, aryl triflate would be more favorable to ipso substitution. Fluorescence spectroscopy and cyclic voltammetry investigations suggest that the interaction between excited acetone and aryl triflate is essential to these couplings. The results in this report are anticipated to provide new opportunities to perform cross-couplings.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions

The direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions has been developed. The reported protocol is practical and represents an efficient method to produce functionalized amides in moderate to good yields.

A to aryl diazonium tetrafluoroborate salts with a nitrile preparation machine acid radical amine compounds (by machine translation)

The invention provides a high-efficiency, high-selective synthesis of different substituted functional group containing organic amide compound, it adopts the cuprous iodide as a catalyst, in order to aryl diazonium tetrafluoroborate salts compounds and organic nitrile compound as the reaction substrate, the reaction system by adding the organic solvent, water and alkali. The advantage of this method: cheap and easily obtained catalyst; the substrate has a high applicability; mild reaction conditions, safe and reliable; the resulting target product selectivity is close to 100%, yield is as high as 90% or more. The method solves the traditional synthetic organic amide compound of rigorous reaction conditions, the reaction selectivity is poor, the experimental procedure is complicated, the productivity is low and needs to be used for the environment of a harmful reagent and the like, it has good industrial application prospect. The invention also provides a corresponding different substituted functional group containing organic amide compound. (by machine translation)