3421-18-9

Basic information

• Product Name: 2,5-di(morpholin-4-yl)cyclohexa-2,5-diene-1,4-dione
• Synonyms: 2,5-Cyclohexadiene-1,4-dione, 2,5-di-4-morpholinyl-; 2,5-Di(morpholin-4-yl)-1,4-benzoquinone
• CAS NO: 3421-18-9
• Molecular Formula: C₁₄H₁₈N₂O₄
• Molecular Weight: 278.3037
• Mol File: 3421-18-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 455.8°C at 760 mmHg
• Flash Point: 229.4°C
• Density: 1.348g/cm³
• Vapor Pressure: 1.71E-08mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: 2,5-di(morpholin-4-yl)cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-di(morpholin-4-yl)cyclohexa-2,5-diene-1,4-dione(3421-18-9)
• EPA Substance Registry System: 2,5-di(morpholin-4-yl)cyclohexa-2,5-diene-1,4-dione(3421-18-9)

Safety Data

• Hazardous Substances Data: 3421-18-9(Hazardous Substances Data)

Usage

Type of compound

Chemical compound

Structure

Cyclic compound containing two morpholine groups and a diene-1,4-dione moiety

Potential applications

Organic chemistry, material science, synthesis of various organic compounds and polymers, pharmacological applications

Unique features

Versatile chemical compound with diverse potential applications in scientific research and industry

Upstream product

• 110-91-8 morpholine 
• 7732-18-5 water 
• 7722-84-1 dihydrogen peroxide 
• 108-95-2 phenol 
• 121-33-5 vanillin 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 4733-50-0 2,3-dicyano-1,4-hydroquinone 
• 150786-25-7 1,4-Dichlor-3-hydroxy-8a-morpholin-4-yl-5,6,7,8a-tetrahydro-<4bH>-dibenzofuran-8-on 
• 106-51-4 p-benzoquinone 
• 67-56-1 methanol 
• 123-31-9 hydroquinone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 526-62-5 2,5-bis(1-aziridinyl)-1,4-benzoquinone 

Downstream Products

• 384377-28-0 2,5-dimorpholino-3,6-bis(phenylthio)cyclohexa-2,5-diene-1,4-dione 
• 1413935-99-5 diethyl 2,2'-(2,5-dimorpholino-3,6-dioxocyclohexa-1,4-diene-1,4-diyl)bis(sulfanediyl)diacetate 

Relevant articles and documents

Crystal Structure of Morpholinium-2,3-dicyano-hydroquinolate [1]

On deprotonation of 2,3-dicyano-p-hydroquinone by morpholine, a network of hydrogen bonds is formed in which the chains of hydroquinone monoanions are connected by strong ⊕N H...O and by weak ⊕N H...N bonds via the morpholinium nitrogens.

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.