32954-65-7

Basic information

• Product Name: N-(acetyloxy)-N-phenylacetamide
• CAS NO: 32954-65-7
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.1992
• Mol File: 32954-65-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 271.6°C at 760 mmHg
• Flash Point: 118.1°C
• Density: 1.199g/cm³
• Vapor Pressure: 0.00638mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: N-(acetyloxy)-N-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(acetyloxy)-N-phenylacetamide(32954-65-7)
• EPA Substance Registry System: N-(acetyloxy)-N-phenylacetamide(32954-65-7)

Safety Data

• Hazardous Substances Data: 32954-65-7(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 
• 586-96-9 Nitrosobenzene 
• 1795-83-1 N-Phenylacetohydroxamic acid 
• 75-36-5 acetyl chloride 
• 3451-88-5 1,1'-Diacetyl-1,1',4,4'-tetrahydro-4,4'-bipyridine 

Downstream Products

• 1795-83-1 N-Phenylacetohydroxamic acid 
• 100-65-2 N-Phenylhydroxylamine 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 99290-14-9 1-(3-ethyl-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 78388-92-8 1-(3-methyl-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 1610681-59-8 1-[2-(4-methoxyphenyl)-3-phenylindol-1-yl]ethanone 
• 5782-02-5 1-(2,3-bis(4-methoxyphenyl)-1H-indol-1-yl)ethanone 
• 3469-20-3 2,3-diphenyl-1H-indole 
• 1239-56-1 1-(2,3-diphenyl-1H-indol-1-yl)ethan-1-one 

Relevant articles and documents

Rhodium-Catalyzed Annulation of N-Acetoxyacetanilide with Substituted Alkynes: Conversion of Nitroarenes to Substituted Indoles

A general and efficient rhodium-catalyzed redox-neutral annulation of N-acetoxyacetanilides, readily accessible from nitroarenes, with alkynes has been accomplished for the synthesis of substituted indole derivatives. A wide range of substituted 2,3-diarylindoles were achieved from various substituted N-acetoxyacetanilides and symmetrical/unsymmetrical alkynes in good to excellent yields. The developed method was successfully integrated with the synthesis of N-acetoxyacetanilides for the efficient one-pot synthesis of indoles from nitroarenes. The important features are the introduction of N-acetoxyacetamide as a new directing group, redox-neutral annulation, an additive-free approach, wide functional group tolerance, an intramolecular version, and a one-pot reaction of nitroarenes. The method was further extended to the synthesis of potent higher analogues of indole, viz., pyrrolo[3,2-f]indoles and dibenzo[a,c]carbazoles. In addition, a plausible mechanism was proposed based on the isolation and stoichiometric study of a potential aryl-Rh intermediate.

Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides

N-Arylacetamides were prepared in excellent yields from nitroarenes in the presence of acetic anhydride, acetic acid and indium by a one-pot procedure.

A novel one pot reductive acetylation of nitroarenes

Nitroarenes are reductively acetylated in one pot to the corres, ponding N-arylacetamides and N-(acetyloxy)-N-arylacetamides with Zn and Ac2O in presence of acidic Al2O3 in dichloromethane at room temperature.