1521-06-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2,5-Diamino-2,5-cyclohexadiene-1,4-dione is used as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure and reactivity allow for the creation of a wide range of molecules with potential therapeutic applications.
Used in Materials Science and Polymer Chemistry:
In the field of materials science, 2,5-Diamino-2,5-cyclohadiene-1,4-dione is utilized for its ability to form stable complexes with metal ions, making it a valuable component in the development of advanced materials. Additionally, its conjugated system contributes to its potential use in polymer chemistry, where it can be incorporated into polymer structures to impart specific properties.
Used in Anticancer Research:
2,5-Diamino-2,5-cyclohexadiene-1,4-dione is being investigated for its potential as an anticancer agent. Its unique structure and reactivity may allow it to interact with biological targets in ways that could inhibit cancer cell growth or induce cell death, making it a promising candidate for further research and development in oncology.
Used in Antifungal Applications:
2,5-Diamino-2,5-cyclohexadiene-1,4-dione is also being studied for its potential as an antifungal agent. Its ability to form complexes and its reactivity may contribute to its effectiveness against fungal infections, offering a new avenue for the development of antifungal treatments.

InChI:InChI=1/C6H6N2O2/c7-3-1-5(9)4(8)2-6(3)10/h1-2H,7-8H2

Upstream product

• 3117-03-1 2,5-dimethoxyquinone 
• 27344-26-9 3,6-diamino-2,5-dibromo-1,4-benzoquinone 
• 488-48-2 tetrabromobenzoquinone 
• 2641-89-6 2,3,5,6-tetrabromohydroquinone 
• 59997-00-1 N,N'-(hydroxy-p-phenylene)-bis-acetamide 
• 123-31-9 hydroquinone 
• 21086-65-7 4,5-dimethoxy-1,2-benzoquinone 
• 106-51-4 p-benzoquinone 
• 24171-03-7 2,5-Diamino-1,4-benzenediol bis hydrochloride 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 2046-89-1 N,N'-(3,6-dioxocyclohexa-1,4-diene-1,4-diyl)diacetamide 

Downstream Products

• 2046-89-1 N,N'-(3,6-dioxocyclohexa-1,4-diene-1,4-diyl)diacetamide 
• 59013-30-8 2,5-Diaminohydroquinone tetraacetate 
• 51073-99-5 2,6-di-p-tolyl-benzo[1,2-d;4,5-d']bisoxazole 
• 43036-58-4 2,6-diphenylbenzo[1,2-d:4,5-d']bis(oxazole) 
• 43036-59-5 2,2'-benzo[1,2-d;4,5-d']bisoxazole-2,6-diyl-bis-phenol 
• 24118-33-0 2,5-bis-benzoylamino-[1,4]benzoquinone 
• 51073-94-0 2,6-bis-(4-methoxy-phenyl)-benzo[1,2-d;4,5-d']bisoxazole 
• 115121-31-8 3,7-dihydro-benzo[1,2-d;4,5-d']bisoxazole-2,6-dithione 
• 10325-89-0 2,5-diamino-1,4-benzenediol 
• 615-94-1 2,5-dihydroxy-1,4-benzoquinone 

Relevant academic research and scientific papers

An efficient synthesis of 2,5-diamino-1,4-benzoquinone

A novel and efficient synthesis of 2,5-diamino-1,4-benzoquinone is described. The reaction involves a palladium/charcoal hydrogenolysis as the key step and provides the desired product in only four steps and very good overall yield. Georg Thieme Verlag Stuttgart.

A Strategic High Yield Synthesis of 2,5-Dihydroxy-1,4-benzoquinone Based MOFs

Metal organic frameworks (MOFs) of the type NBu4M(DHBQ)1.5 (M = Ni2+, Fe2+, and Co2+ DHBQ = 2,5-dihydroxy-1,4-benzoquinone) were prepared with improved yield up to 100% via a simple benchtop aqueous addition reaction. For the first time, the crystalline phase of this formula polymer was synthesized without in situ generation of the DHBQ ligand from 2, 5-diamino-1,4-benzoquinone (DABQ). Powder X-ray diffraction and elemental analysis confirm the crystalline phase and composition of products. Infrared and electron dispersive spectroscopy further confirm that the materials are homologous to the reported single crystalline polymers. The present MOF synthesis can be extended to halide-substituted ligands, i.e., 3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone (chloranilic acid, CAN) and 3,6-difluoro-2,5-dihydroxy-1,4-benzoquinone (fluoranilic acid, FAN).

A H-bond stabilized quinone electrode material for Li-organic batteries: The strength of weak bonds

Small organic materials are generally plagued by their high solubility in battery electrolytes. Finding approaches to suppress solubilization while not penalizing gravimetric capacity remains a challenge. Here we propose the concept of a hydrogen bond stabilized organic battery framework as a viable solution. This is illustrated for 2,5-diamino-1,4-benzoquinone (DABQ), an electrically neutral and low mass organic chemical, yet with unusual thermal stability and low solubility in battery electrolytes. These properties are shown to arise from hydrogen bond molecular crystal stabilization, confirmed by a suite of techniques including X-ray diffraction and infrared spectroscopy. We also establish a quantitative correlation between the electrolyte solvent polarity, molecular structure of the electrolyte and DABQ solubility-then correlate these to the cycling stability. Notably, DABQ displays a highly reversible (above 99%) sequential 2-electron electrochemical activity in the solid phase, a process rarely observed for similar small molecular battery chemistries. Taken together, these results reveal a potential new strategy towards stable and practical organic battery chemistries through intramolecular hydrogen-bonding crystal stabilization.

Synthesis of diamino benzoquinones using facile and one-pot chemical oxidative method

An efficient synthesis of diamino benzoquinone, beginning from catechol derivatives and hydroquinone with azide ion was developed in the presence of potassium ferricyanide as an oxidizing agent (Decker oxidation), the results of which revealed the partici

Synthesis, characterization, spectral property, Hirshfeld surface analysis and TD/DFT calculations of 2, 6-disubstituted benzobisoxazoles

An effective and clean aerobic oxidative method for the synthesis of 2,6-disubstituted benzobisoxazole using the free radical catalysis was obtained. 2, 6-Di(pyridin-4-yl)-benzo[1,2-d:4,5-d']bisoxazole was synthesized and characterized by 1H an

Quinone Compound-Graphene Composite Material, Preparation Method Thereof, and Flexible Lithium Secondary Battery

A quinone compound-graphene composite material, including quinone compound and graphene, where the quinone compound is chemically bonded on the surface of the graphene, and the quinone compound is quinone compound monomer or quinone polymer. The quinone compound-graphene composite material has high energy density, high flexibility, high conductivity, and high stability, and can be used as cathode material for preparing flexible electrode. Additionally, a preparation method of quinone compound-graphene composite material, and flexible lithium secondary battery uses the quinone compound-graphene composite material as cathode active material.

Straightforward synthesis of substituted p-Quinones: Isolation of a key intermediate and use as a bridging ligand in a diruthenium complex

(Figure Presented) Keep it simple: A new transamination method is reported for the synthesis of diamino-substituted p-quinones (see scheme). Asymmetrically substituted p-quinones are shown to be key intermediates in this reaction. The redox properties of these ligands are discussed and their utility in coordination and redox chemistry is shown with a representative example.

Investigation of electrochemically induced Michael addition reactions. Oxidation of some dihydroxybenzene derivatives in the presence of azide ion

In aqueous solution containing azide ion as a nucleophile, electrochemical oxidation of hydroquinone and some dihydroxybenzoic acids have been studied using cyclic voltammetry and controlled-potential coulometry. The voltammetric data show that electroche