1521-03-5

Basic information

• Product Name: 2,5-di(pyrrolidin-1-yl)cyclohexa-2,5-diene-1,4-dione
• Synonyms: 2,5-di(pyrrolidin-1-yl)cyclohexa-2,5-diene-1,4-dione
• CAS NO: 1521-03-5
• Molecular Weight: 246.309
• Mol File: 1521-03-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,5-di(pyrrolidin-1-yl)cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-di(pyrrolidin-1-yl)cyclohexa-2,5-diene-1,4-dione(1521-03-5)
• EPA Substance Registry System: 2,5-di(pyrrolidin-1-yl)cyclohexa-2,5-diene-1,4-dione(1521-03-5)

Safety Data

• Hazardous Substances Data: 1521-03-5(Hazardous Substances Data)

Upstream product

• 123-75-1 pyrrolidine 
• 121-33-5 vanillin 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 156908-76-8 2-chloro-5-(pyrrolidin-1-yl)cyclohexa-2,5-diene-1,4-dione 
• 106-51-4 p-benzoquinone 

Relevant articles and documents

Unprecedented Formation of 2,5-Diaminoquinones from the Reaction of Vanillin with Secondary Amines in Aerobic Conditions

Vanillin is widely used as a flavoring agent in foods, perfumes and in several other applications. Even if huge amounts of vanillin are annually employed in these manufacturing processes, its reactivity is underexplored, especially for the formation of potentially toxic substances. In this context, we observed the formation of orange to red crystalline compounds in the reaction of vanillin with secondary amines in aerobic conditions. NMR and HRMS allowed identifying the products as 2,5-diamino-1,4-benzoquinones. Preliminary investigations of this reaction led to a proposed mechanism involving an oxidative fragmentation of vanillin as the key step. MTT tests did not show any toxic effect up to 0.1 mm.

Cine-substitution in reactions of dichloro-1,4-benzoquinones with pyrrolidine

Products of cine-substitution are formed in reactions of 2,5- and 2,6-dichloro-1,4-benzoquinones with pyrrolidine. The main reason for amination of chloroquinones by pyrrolidine via the mechanism of cine-substitution is the high basicity of this amine. A high degree of localization of the π-bond in the molecules of the starting chloroquinones and the strong conjugation of the amino group with the quinone ring in the molecules of the intermediate monoaminoquinones are two other factors that favor an increase in yields of the products of cine-substitution.