6312-87-4

Basic information

• Product Name: N-(4-PHENOXY-PHENYL)-ACETAMIDE
• Synonyms: N-(4-PHENOXY-PHENYL)-ACETAMIDE;Ccris 7394;N-(4-Phenoxyphenyl)
• CAS NO: 6312-87-4
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.25852
• Mol File: 6312-87-4.mol

Chemical Properties

• Melting Point: 106-107 °C
• Boiling Point: 410.8 °C at 760 mmHg
• Flash Point: 202.2 °C
• Appearance: /
• Density: 1.176 g/cm³
• Vapor Pressure: 5.87E-07mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.36±0.70(Predicted)
• CAS DataBase Reference: N-(4-PHENOXY-PHENYL)-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-PHENOXY-PHENYL)-ACETAMIDE(6312-87-4)
• EPA Substance Registry System: N-(4-PHENOXY-PHENYL)-ACETAMIDE(6312-87-4)

Safety Data

• Hazardous Substances Data: 6312-87-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(4-PHENOXY-PHENYL)-ACETAMIDE is used as a key intermediate for the synthesis of various organic molecules, contributing to the development of new chemical entities with diverse applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, N-(4-PHENOXY-PHENYL)-ACETAMIDE is utilized as a building block for the creation of novel drug candidates, potentially leading to the discovery of new therapeutic agents with improved efficacy and safety profiles.
Used in Medicinal Chemistry:
N-(4-PHENOXY-PHENYL)-ACETAMIDE is being explored for its potential biological activities, with the aim of identifying its role in medicinal chemistry and its applicability in the treatment or management of various diseases and conditions.

InChI:InChI=1/C14H13NO2/c1-11(16)15-12-7-9-14(10-8-12)17-13-5-3-2-4-6-13/h2-10H,1H3,(H,15,16)

Upstream product

• 539-03-7 N-(4-chlorophenyl)acetamide 
• 108-95-2 phenol 
• 103-88-8 4-bromoacetanilide 
• 108-86-1 bromobenzene 
• 103-90-2 4-acetaminophenol 
• 14040-11-0 tungsten hexacarbonyl 
• 620-88-2 4-nitrophenyl phenyl ether 
• 616-38-6 carbonic acid dimethyl ester 
• 6337-25-3 1-(4-phenoxy-phenyl)-ethanone oxime 
• 6337-25-3 1-(4-phenoxyphenyl)ethan-1-one oxime 
• 75-05-8 acetonitrile 
• 139-59-3 4-phenoxyanilin 
• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 

Downstream Products

• 274902-58-8 N-(4-phenoxy-phenyl)-N-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-acetamide 
• 171349-99-8 N-ethyl-4-phenoxyaniline 
• 1120334-11-3 2-bromo-6-nitro-4-phenoxyphenylamine 
• 139-59-3 4-phenoxyanilin 
• 1613336-62-1 3,5-diiodo-2-methoxy-N-methyl-N-(4-phenoxyphenyl)benzamide 
• 1613336-61-0 2-hydroxy-3,5-diiodo-N-methyl-N-(4-phenoxyphenyl)benzamide 
• 72920-03-7 para-phenoxy-N-methylaniline 
• 92163-23-0 2-methyl-6-phenoxy-benzothiazole 
• 315248-48-7 N-acetyl-sulfanilic acid-(4-phenoxy-anilide) 
• 855761-40-9 8-nitro-6-phenoxy-quinoline 
• 855837-35-3 6-phenoxy-[8]quinolylamine 
• 58518-73-3 4-(4-iodo-phenoxy)-aniline 
• 620-55-3 1-nitro-3-phenoxybenzene 

Relevant articles and documents

A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds

Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism

Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.

Visible-light-induced Beckmann rearrangement by organic photoredox catalysis

A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.

Synthesis, structure-activity relationship and molecular docking studies of novel quinoline-chalcone hybrids as potential anticancer agents and tubulin inhibitors

A new series of quinoline-chalcone hybrids was synthesized. The structures of these compounds were characterized by spectroscopic methods including 1H and 13CNMR and mass spectroscopy. The cytotoxic activity of compounds was evaluated against four human cancer cell lines including A2780 (human ovarian carcinoma) and A2780/RCIS (Cisplatin resistant human ovarian carcinoma), MCF-7 (human breast cancer cells), MCF-7/MX (Mitoxantrone resistant human breast cancer cells) and normal Huvec cells. The structure-activity relationship of synthesized compounds is discussed. Among quinolines 5e, 5g and 5j possessing benzoyl group showed significant cytotoxic activity against both resistant cancer cells and their parents. Compounds 5g and 5j, demonstrated the most antiproliferative activity with IC50 values ranging from 2.32 to 22.4 μM. They were also identified as tubulin inhibitors and induced cell cycle arrest at G2/M phase and apoptosis. Compound 5j induced more arrest at G2/M phase in four cancer cell lines compared to compound 5g. Finally, molecular dynamics simulation and molecular docking studies of compound 5j into the colchicine-binding site of tubulin demonstrated the possible interaction of this compound in the active site of tubulin.

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

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)

Photo-Fries rearrangement of aryl acetamides: Regioselectivity induced by the aqueous micellar green environment

Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be a powerful synthetic tool when it is possible to conduct it in regioselective conditions yielding a single photoproduct. Water-surfactant solutions as reaction media can be considered as an approach in this context because they show products with different features than those from isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C-N bond to yield a singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radical pair, resulting in noticeable photoproduct selectivity.

Metal-free n -arylation of secondary amides at room temperature

The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.