1521-04-6

Basic information

• Product Name: 2,5-di(piperidin-1-yl)cyclohexa-2,5-diene-1,4-dione
• Synonyms: p-Benzoquinone, 2,5-dipiperidino-
• CAS NO: 1521-04-6
• Molecular Formula: C₁₆H₂₂N₂O₂
• Molecular Weight: 274.3581
• Mol File: 1521-04-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 423°C at 760 mmHg
• Flash Point: 183.3°C
• Density: 1.222g/cm³
• Vapor Pressure: 2.3E-07mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: 2,5-di(piperidin-1-yl)cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-di(piperidin-1-yl)cyclohexa-2,5-diene-1,4-dione(1521-04-6)
• EPA Substance Registry System: 2,5-di(piperidin-1-yl)cyclohexa-2,5-diene-1,4-dione(1521-04-6)

Safety Data

• Hazardous Substances Data: 1521-04-6(Hazardous Substances Data)

Usage

Type of compound

cyclic enaminone derivative

Structure

two piperidine groups attached to a cyclohexadienedione ring

Potential uses

building block for organic compounds and materials, pharmaceuticals, dyes, functional materials, ligand for transition metal complexes in catalytic applications.

Upstream product

• 110-89-4 piperidine 
• 67-56-1 methanol 
• 526-62-5 2,5-bis(1-aziridinyl)-1,4-benzoquinone 
• 20765-04-2 2,5-diethoxy-[1,4]benzoquinone 
• 106-51-4 p-benzoquinone 
• 121-33-5 vanillin 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 615-94-1 2,5-dihydroxy-1,4-benzoquinone 
• 123-31-9 hydroquinone 

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.

Synthesis of 2,5-Diaminoquinones by one-pot copper-catalyzed aerobic oxidation of hydroquinones and addition reaction of amines

The aerobic oxidation of various hydroquinones was achieved by using copper nanoparticles entrapped in aluminum oxyhydroxide [Cu/ AlO(OH)] at room temperature. Furthermore, 2,5diamino-1,4-benzoquinones were synthesized directly from hydroquinone and amines by a one-pot procedure consisting of the copper-catalyzed aerobic oxidation of hydroquinones and the double addition of amines to the resulting quinones.