14289-45-3

Basic information

• Product Name: 2-Naphthaleneacetic acid, a-oxo-
• CAS NO: 14289-45-3
• Molecular Formula: C12H8O3
• Molecular Weight: 200.194
• Mol File: 14289-45-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-Naphthaleneacetic acid, a-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthaleneacetic acid, a-oxo-(14289-45-3)
• EPA Substance Registry System: 2-Naphthaleneacetic acid, a-oxo-(14289-45-3)

Safety Data

• Hazardous Substances Data: 14289-45-3(Hazardous Substances Data)

Upstream product

• 33741-78-5 DL-2-Amino-2-(2-naphthyl)acetic acid 
• 21473-01-8 2-naphthalenylmagnesium bromide 

Downstream Products

• 66-99-9 β-naphthaldehyde 
• 170166-53-7 methyl 2'-naphthoylformate 
• 1762-15-8 1-(naphthalen-2-yl)-2-phenylethanone 
• 43210-73-7 (R)-2-hydroxy-2-(2-naphthyl)acetic acid 
• 136935-71-2 β-naphthyl-4-methylphenyl-ketone 
• 1228377-98-7 N-methyl-2-(naphthalen-2-yl)-2-oxo-N-phenylacetamide 
• 887641-75-0 benzyl 2-(naphthalen-3-yl)-2-oxoacetate 

Relevant articles and documents

Diphenylparabanic acid as a synthon for the synthesis of α-diketones and α-ketocarboxylic acids

Diphenylparabanic acid was found to react with >2 equiv of organolithiums at -78 °C to effectively give the corresponding symmetrical α-diketones. However, upon treatment with 1 equiv of organolithium, the parabanic acid gave mainly 5-substituted 5-hydroxyimidazolidine-2,4-diones. On the other hand, Grignard reagents were less reactive toward the parabanic acid at low temperature, and selectively gave the corresponding 5- hydroxyimidazolidine-2,4-diones even if more than 1 equiv of the reagents was used. A tandem process in which the parabanic acid was first reacted with a Grignard reagent and then reacted in one-pot with an organolithium effectively gave the unsymmetrical α-diketone. 5-Substituted 5-hydroxyimidazolidine-2, 4-diones were useful as versatile precursors for preparing α- ketocarboxylic acids as well as unsymmetrical α-diketones.