10286-75-6

Basic information

• Product Name: N-(3,4-Dichlorophenyl)benzamide
• Synonyms: N-(3,4-Dichlorophenyl)benzamide;3',4'-DICHLOROBENZANILIDE
• CAS NO: 10286-75-6
• Molecular Formula: C₁₃H₉Cl₂NO
• Molecular Weight: 266.1227
• Mol File: 10286-75-6.mol

Chemical Properties

• Melting Point: 145-146 °C
• Boiling Point: 304.7°Cat760mmHg
• Flash Point: 138.1°C
• Appearance: /
• Density: 1.384g/cm³
• Vapor Pressure: 0.00086mmHg at 25°C
• Refractive Index: 1.656
• PKA: 11.97±0.70(Predicted)
• CAS DataBase Reference: N-(3,4-Dichlorophenyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,4-Dichlorophenyl)benzamide(10286-75-6)
• EPA Substance Registry System: N-(3,4-Dichlorophenyl)benzamide(10286-75-6)

Safety Data

• Hazardous Substances Data: 10286-75-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H9Cl2NO/c14-11-7-6-10(8-12(11)15)16-13(17)9-4-2-1-3-5-9/h1-8H,(H,16,17)

Upstream product

• 6004-21-3 3'-chloro-benzanilide 
• 20555-91-3 3,4-dichloroiodobenzene 
• 100-47-0 benzonitrile 
• 932-90-1 Benzaldoxime 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 151169-75-4 3,4-dichlophenylboronic acid 
• 2399-66-8 1-benzoylpyrrolidin-2-one 
• 95-76-1 m,p-dichloroaniline 
• 99-54-7 3,4-dichloronitrobenzene 
• 65-85-0 benzoic acid 
• 71144-20-2 (3,4-Dichloranilino)phenyl-acetonitril 
• 98-88-4 benzoyl chloride 

Downstream Products

• 344250-20-0 N-(3,4-dichlorophenyl)benzimidoyl chloride 
• 95-76-1 m,p-dichloroaniline 
• 100-51-6 benzyl alcohol 
• 666175-14-0 1-[(3,4-dichlorophenylimino)phenylmethyl]-3-ethylthiourea 
• 10278-50-9 3',4'-dichlorothiobenzanilide 

Relevant articles and documents

Copper-catalyzed regioselective synthesis of N-aryl amides from aldoximes and aryl halides

Ligand-assisted copper-catalyzed reaction of aldoximes with aryl halides is described for the regioselective synthesis of N-aryl amides. This protocol is simple and compatible with a wide range of functional groups attached to the aryl ring of the halides as well as aldoximes. Copyright

Discovery and Mechanism of Action of Small Molecule Inhibitors of Ceramidases**

Sphingolipid metabolism is tightly controlled by enzymes to regulate essential processes in human physiology. The central metabolite is ceramide, a pro-apoptotic lipid catabolized by ceramidase enzymes to produce pro-proliferative sphingosine-1-phosphate. Alkaline ceramidases are transmembrane enzymes that recently attracted attention for drug development in fatty liver diseases. However, due to their hydrophobic nature, no specific small molecule inhibitors have been reported. We present the discovery and mechanism of action of the first drug-like inhibitors of alkaline ceramidase 3 (ACER3). In particular, we chemically engineered novel fluorescent ceramide substrates enabling screening of large compound libraries and characterized enzyme:inhibitor interactions using mass spectrometry and MD simulations. In addition to revealing a new paradigm for inhibition of lipid metabolising enzymes with non-lipidic small molecules, our data lay the ground for targeting ACER3 in drug discovery efforts.

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions

N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.

Copper-Catalyzed Regioselective Synthesis of N-Aryl Amides from Aldoximes and Aryl Halides

Ligand-assisted copper-catalyzed reaction of aldoximes with aryl halides is described for the regioselective synthesis of N-aryl amides. This protocol is simple and compatible with a wide range of functional groups attached to the aryl ring of the halides as well as aldoximes.

Copper catalyzed N-arylation between aryl halides and nitriles in water: An efficient tandem synthesis of benzanilides

A series of benzanilide compounds were synthesized through copper-catalyzed tandem reactions. With the assistance of ionic liquid as phase transfer catalyst, aryl halides, and nitriles underwent a hydrolysis/coupling pathway to form benzanilides in water. Advantages of this reaction include the use of water as the environmental friendly solvent, short reaction time, and the tolerance of various functional groups. A proposed mechanism based on control experiments is also presented.

A novel synthesis of N-arylamides from nitroarenes via reductive N-acylation with red phosphorus and iodine

A series of N-arylamides and imides were synthesized via reductive N-acylation of nitroarenes with red phosphorus and carboxylic acids, catalyzed by iodine or iodides; an I /I° redox cycle was proposed to promote the reaction. Georg Thieme Verlag Stuttgart.

Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors

A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [3H]CCPA to human A1 adenosine receptors, whereas modest and varying effects were observed on the binding of [3H]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A2A and A3 receptors. Compounds 7a and 7l displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A2A receptors, whereas 7a showed some activity on A3 receptors.