153280-10-5

Basic information

• Product Name: (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one
• Synonyms: (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one
• CAS NO: 153280-10-5
• Molecular Weight: 191.186
• Mol File: 153280-10-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one(153280-10-5)
• EPA Substance Registry System: (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one(153280-10-5)

Safety Data

• Hazardous Substances Data: 153280-10-5(Hazardous Substances Data)

Upstream product

• 517-21-5 glyoxal sodium bisulfite 
• 100-52-7 benzaldehyde 
• 151-50-8 potassium cyanide 

Downstream Products

• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 23064-32-6 3,4-Dihydroxy-5-phenyl-2(5H)-furanon 
• 133373-27-0 2,2-dihydroxy-3-oxo-4-phenylbutanamide 
• 828-01-3 phenyllactic acid 

Relevant articles and documents

Facile structural elucidation of imidazoles and oxazoles based on NMR spectroscopy and quantum mechanical calculations

The reaction of 1,2,3-tricarbonyl derivatives with hexamethylenetetramine and ammonium acetate in acetic acid provides an unambiguous approach to the synthesis of imidazoles, whereas the Bredereck reaction of α-haloketones in formamide, yields both imidazoles and oxazoles. Herein we describe a facile methodology for distinguishing between these heterocyclic compounds based on a combination of NMR spectroscopy and quantum mechanical calculations. In the NMR data the oxazole C-2 has a chemical shift of ca. 150 ppm whereas in the imidazoles it is found at ca. 135 ppm, with a 1JC-H of ca. 250 Hz for the oxazoles and ca. 210 Hz for the imidazoles. 1JC-H values can be easily obtained from a gated-decoupled 13C spectrum, and even more trivially, from the separation of the H-2 13C satellites in the 1H spectra. Additionally, the computed NMR data, obtained from density functional theory, are found to be in good agreement with the experimental data and serve as valuable tools in identifying the products of the Bredereck reaction.

Unstable 1,1,2-Enetriols as (Probable) Intermediates in the Decarboxylation of α,β-Diketo Acids

During the acid hydrolysis of (hydrated) 4-aryl-2,3-diketobutyramide 2 (aryl = phenyl, o-chlorophenyl, p-methoxyphenyl), 3-aryllactic acid (5) is formed by rapid decarboxylation of the intermediate diketo acid (3).In the decarboxylation step, a further unstable intermediate is formed.The latter manifests itself by reducing 1 mol of added iodine during the hydrolysis-decarboxylation reaction, thereby forming 3-arylpyruvic acid (6), isolated instead of 5.Thus, the oxidation of the unstable intermediate by iodine is more rapid than its ketonization.It is formulated as an 1,1,2-enetriol (4), more probably than an α-hydroxyketone.