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

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 
• 123-31-9 hydroquinone 
• 106-51-4 p-benzoquinone 
• 615-94-1 2,5-dihydroxy-1,4-benzoquinone 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 121-33-5 vanillin 

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.

Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones "in-Water" and their biological evaluation as antibacterial and antifungal agents

Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio)cyclohexa-2,5-diene-1,4-diones (4d-14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa- 2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst "In-Water" by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929.

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.

Kinetics and Mechanism of Molecular Interaction between 1,4-Benzoquinone and Piperidine

Kinetics of formation of a charge transfer (CT) complex, between 1,4-benzoquinone and piperidine in chloroform and the transformation of the complex to the final product have been investigated spectrophotometrically.The product has been isolated and characterised as 2,5-dipiperidino-1,4-benzoquinone by IR, PMR and elemental analyses.A mechanism consistent with the experimental results, involving an intermediate formation between CT and product has been postulated.