5257-06-7

Basic information

• Product Name: N-(2-ACETYLPHENYL)FORMAMIDE
• Synonyms: N-(2-ACETYLPHENYL)FORMAMIDE;formylaminoacetophenone;2-Acetyl-N-formylaniline
• CAS NO: 5257-06-7
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• Mol File: 5257-06-7.mol
• Article Data: 53

Chemical Properties

• Melting Point: 65 °C
• Boiling Point: 359.1°C at 760 mmHg
• Flash Point: 168.3°C
• Appearance: /
• Density: 1.184g/cm³
• Vapor Pressure: 2.43E-05mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: N-(2-ACETYLPHENYL)FORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-ACETYLPHENYL)FORMAMIDE(5257-06-7)
• EPA Substance Registry System: N-(2-ACETYLPHENYL)FORMAMIDE(5257-06-7)

Safety Data

• Hazardous Substances Data: 5257-06-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 36, p. 462, 1988 DOI: 10.1248/cpb.36.462

InChI:InChI=1/C9H9NO2/c1-7(12)8-4-2-3-5-9(8)10-6-11/h2-6H,1H3,(H,10,11)

Upstream product

• 87-51-4 indole-3-acetic acid 
• 551-93-9 2-aminoacetophenone 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 83-34-1 3-Methylindole 
• 29189-60-4 (5,10,15,20-tetraphenylporphyrinato)Fe(THF)2 
• 822-36-6 4-methyl-1H-imidazole 
• 75-91-2 tert.-butylhydroperoxide 
• 95-53-4 o-toluidine 
• 1895-39-2 sodium chlorodifluoroacetate 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 75-05-8 acetonitrile 
• 123-91-1 1,4-dioxane 
• 68-12-2 N,N-dimethyl-formamide 
• 2258-42-6 formyl acetic anhydride 

Downstream Products

• 1451070-60-2 3-benzyl-4-methylene-3,4-dihydroquinazoline 
• 1451070-61-3 3-(4-methylbenzyl)-4-methylene-3,4-dihydroquinazoline 
• 1451070-62-4 3-(4-chlorobenzyl)-4-methylene-3,4-dihydroquinazoline 
• 1451070-63-5 C₁₇H₁₆N₂O 
• 1451070-64-6 3-(2,4-dimethoxybenzyl)-4-methylene-3,4-dihydroquinazoline 
• 5388-11-4 3-benzyl-3H-quinazolin-4-one 
• 141305-99-9 3-(4-methoxybenzyl)quinazolin-4(3H)-one 
• 55276-35-2 phenyl(quinazolin-4-yl)methanone 
• 55326-10-8 (4-methoxyphenyl)(quinazolin-4-yl)methanone 
• 551-93-9 2-aminoacetophenone 
• 106795-49-7 N-[2-(1-hydroxyethyl)phenyl]formamide 
• 1644428-71-6 1-(1-azidoethyl)-2-isocyanobenzene 
• 1644428-63-6 N-[2-(1-azidoethyl)phenyl]formamide 
• 92736-35-1 4-Methyl-1-(4-nitro-benzoyl)-1,2-dihydro-quinazoline-2-carbonitrile 

Relevant articles and documents

Photooxidation of tryptophan leading to 2-Aminoacetophenone - A possible reason for the untypical aging off-flavor in wine

2-Aminoacetophenone (AAP) was recognized as the key compound for the so-called untypical aging off-flavor (UTA) in Vitis vinifera wines. In this study, it was shown that AAP can be formed by photooxidation of free and protein-bound tryptophan (TRP) in combination with a subsequent storage in model wine. Solutions of TRP and lysozyme were exposed to artificial sunlight both in the presence and in the absence of the photosensitizer riboflavin. Aliquots of the irradiation batches were stored in model wine solutions containing tartaric acid, sulfite and ethanol in different combinations. AAP formation could be identified from both free and bound (lysozyme) TRP, while free TRP resulted in higher yields. The presence of riboflavin during irradiation generally favored the AAP formation. AAP formation increased with increasing irradiation times, but AAP was not detectable, if TRP was directly incubated in model wine. Not only the irradiation time but also the storage time of model wines favored the formation of AAP. Concerning the model wine composition, it became evident that the presence of tartaric acid resulted in the highest AAP formation during storage.

Photocatalytic Oxidative C-C Bond Cleavage of the Pyrrole Ring in 3-Methylindole induced by Colloidal CdS Particles

Binding of 3-methylindole (3-MI) to the surface of colloidal CdS particles modifies their luminescence Behaviour so that the trapped electron and hole generated upon photoirradiation are scavenged by adsorbed O2 and 3-MI to yield 2-acetylformanilide and 2-aminoacetopnenone.

Organic photoredox catalyzed C-H silylation of quinoxalinones or electron-deficient heteroarenes under ambient air conditions

Direct C-H silylation of quinoxalinones was achieved by the combination of organic photoredox catalysis and hydrogen atom transfer (HAT) under ambient air conditions. Transition metal- and external oxidant-free conditions were the major features of this protocol. A series of silylated quinoxalinones with broad functional groups had been synthesized in moderate to high yields. This methodology was also applicable for the C-H silylation of some electron-deficient heteroarenes.

Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones

Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.