27687-56-5

Basic information

• Product Name: N-hydroxy-N-phenylpropionamide
• Synonyms: N-hydroxy-N-phenylpropionamide
• CAS NO: 27687-56-5
• Molecular Weight: 165.192
• Mol File: 27687-56-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-hydroxy-N-phenylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-N-phenylpropionamide(27687-56-5)
• EPA Substance Registry System: N-hydroxy-N-phenylpropionamide(27687-56-5)

Safety Data

• Hazardous Substances Data: 27687-56-5(Hazardous Substances Data)

Upstream product

• 123-38-6 propionaldehyde 
• 586-96-9 Nitrosobenzene 
• 802294-64-0 propionic acid 
• 600-18-0 2-Oxobutyric acid 
• 79-03-8 propionyl chloride 
• 100-65-2 N-Phenylhydroxylamine 

Downstream Products

• 27688-10-4 N-[2-(2,4-Dichloro-phenoxy)-acetoxy]-N-phenyl-propionamide 
• 27688-26-2 N-Phenyl-N-[2-(2,4,5-trichloro-phenoxy)-propionyloxy]-propionamide 
• 27688-18-2 N-Phenyl-N-[2-(2,4,5-trichloro-phenoxy)-acetoxy]-propionamide 

Relevant articles and documents

N-heterocyclic-carbene-catalyzed one-pot synthesis of hydroxamic esters

The honey pot: The NHC-catalyzed reaction between nitrosobenzenes, aromatic/aliphatic aldehydes, and enals proceeded through an aza-benzoin-type reaction and an internal redox esterification to afford hydroxamic esters in good yields. Copyright

N-Arylhydroxamic Acids: Reaction of Nitroso Aromatics with α-Oxo Acids

A practical and high-yielding route to N-arylhydroxamic acids from nitroso aromatics and α-oxo acids 1a-d is desctibed.In aqueous and acetic acid containing media, the reactions exhibit second-order reaction kinetics overall.In the aqueous medium, the rate constant (kobsd) for N-phenylacetohydroxamic acid (8b) formation increased with increasing +>, though there were some side pathways involving azoxybenzene formation.In general, kobsd for the reaction in the acetic acid containing medium was about one-tenth of that in HCl at pH 0.6.On a preparative scale, acetic acid is better than HCl, in that both reactants showed sufficient solubilities in acetic acid for a high reaction velocity and no side reaction was detected.With this method, the proximate carcinogens, N-(4-biphenylyl)acetohydroxamic acid (12b) and N-(2-fluorenyl)acetohydroxamic acid (13b), could be easily prepared.Under both conditions, the order of kobsd for the reactions of nitrosobenzene (2) with α-oxo acids 1a-d was glyoxylic (1a) > pyruvic (1b) 2-oxobutyric (1c) > benzoylformic (1d) acid.For the reactions of substituted nitrosobenzenes 3-6 with pyruvic acid (1b), the order of kobsd was p-phenyl (6) > unsubstituted (2) > p-chloro (5) > m-chloro (4) >> o-chloro (3) nitrosobenzene.The negative Hammett reaction constant value obtained indicates that an electron-donating substituent is preferable for the reaction.The reaction mechanism and other factors affecting N-arylhydroxamic acid formation are also descussed.