18705-01-6

Basic information

• Product Name: 2-phenoxy-N-phenylacetamide
• Synonyms: acetamide, 2-phenoxy-N-phenyl-
• CAS NO: 18705-01-6
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.2585
• Mol File: 18705-01-6.mol

Chemical Properties

• Boiling Point: 444.2°C at 760 mmHg
• Flash Point: 222.4°C
• Density: 1.19g/cm³
• Vapor Pressure: 4.38E-08mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: 2-phenoxy-N-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenoxy-N-phenylacetamide(18705-01-6)
• EPA Substance Registry System: 2-phenoxy-N-phenylacetamide(18705-01-6)

Safety Data

• Hazardous Substances Data: 18705-01-6(Hazardous Substances Data)

Upstream product

• 5326-87-4 N-(phenyl)bromoacetamide 
• 139-02-6 sodium phenoxide 
• 25774-60-1 2-Phenoxyethansaeure-phenylester 
• 62-53-3 aniline 
• 122-59-8 2-phenoxyacetic acid 
• 701-99-5 Phenoxyacetyl chloride 
• 108-88-3 toluene 
• 108-95-2 phenol 
• 131303-43-0 1-anilino-2,2,2-trichloro-ethanol 
• 587-65-5 N-chloroacetyl-aniline 
• 10397-59-8 N,N-dimethyl-α-phenoxyacetamide 
• 142-04-1 aniline hydrochloride 
• 3598-14-9 phenoxyacetonitrile 
• 66003-76-7 Diphenyliodonium triflate 

Downstream Products

• 3598-16-1 2-phenoxyacetic acid sodium salt 
• 62-53-3 aniline 
• 122-59-8 2-phenoxyacetic acid 
• 122-39-4 diphenylamine 
• 1221-80-3 phenoxy-acetic acid-(N-nitroso-anilide) 

Relevant articles and documents

Synthesis of Some New Acetanilide Derivatives as COX Inhibitors and Assessment of Analgesic/Anti-Inflammatory Activities

The purpose of the present research was to synthesize a new series of acetanilide derivatives that would have analgesic and anti-inflammatory properties in laboratory animals (rats). IR spectroscopy, 1HNMR spectroscopy and Mass spectroscopy wer

An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides

Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram-scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis.

Copper-catalyzed transformation of alkyl nitriles to N -arylacetamide using diaryliodonium salts

This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.

Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement

A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin-like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.

Solvent-free iron(III) chloride-catalyzed direct amidation of esters

Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.

Transformation of lignin model compounds to: N -substituted aromatics via Beckmann rearrangement

Here we present the highly effective cleavage of C-C bonds in lignin model compounds for the production of N-substituted aromatics in up to 96% total yield, including benzonitriles and amides, via oxime formation followed by Beckmann rearrangement (BR). The amides could be further hydrolyzed to anilines (>92% yield) and carboxylic acids (>90% yield), respectively. In addition, the employment of a substrate with a γ-OH group will lead to the formation of C-2 monosubstituted oxazole. A one-pot process involving the BR reaction and hydrolysis has also been developed to directly afford an up to 96% total yield of benzonitriles, benzamides, and anilines. This strategy enabled us to successfully apply the BR reaction to the degradation of lignin model compounds to N-functionalized aromatic products under mild conditions.

The catalytic activity of titania nanostructures in the synthesis of amides under solvent-free conditions

Different shapes and phases of titania nanostructures with the uniform size distribution were synthesized by hydrothermal sol-gel technique. The influence of annealing temperature on the crystalline character, size and phase of the prepared nanomaterials were evidenced from the diffraction analysis. Infrared spectroscopic analysis ensured the structural confirmation of the sulfated titania nanostructures. Catalytic activity of the synthesized nanometric materials in direct amidation of aromatic and aliphatic carboxylic acids with aromatic amines was evaluated. Among the materials studied, sulfated titania nanotubes with the anatase phase exhibited excellent catalytic activity. The employed solvent-free protocol is greener and eradicates the drawbacks associated with the hazardous solvents employed in the prevailing solution phase methodologies.

Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively

We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.

Facile stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones

The highly stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones by the [2+2] cycloaddition of ketenes with imines derived from chloral is described. The highly stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones by the [2+2] cycloaddition of ketenes with imines derived from chloral is described.

A convenient preparation of N-alkyl and N-arylamines by smiles rearrangement - Synthesis of analogues of diclofenac

Smiles rearrangement of substituted aryloxyacetamides in which oxygen and nitrogen are separated by COCH2 group has been successful even when the aryloxy ring carries weak or no electron withdrawing group. Earlier reports of such reactions involved either strong electron withdrawing groups or a special catalyst. The diphenylamines thus obtained gave analogues of diclofenac in only one case.