4622-04-2

Basic information

• Product Name: 2,3-DICYANO-1,4-BENZOQUINONE
• Synonyms: 2,3-DICYANO-1,4-BENZOQUINONE;1,4-Cyclohexadiene-1,2-dicarbonitrile, 3,6-dioxo-;Einecs 225-037-1
• CAS NO: 4622-04-2
• Molecular Formula: C₈H₂N₂O₂
• Molecular Weight: 158.1137
• EINECS: 225-037-1
• Mol File: 4622-04-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 178-180 °C
• Boiling Point: 260.2°Cat760mmHg
• Flash Point: 111.1°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.0124mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 2,3-DICYANO-1,4-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DICYANO-1,4-BENZOQUINONE(4622-04-2)
• EPA Substance Registry System: 2,3-DICYANO-1,4-BENZOQUINONE(4622-04-2)

Safety Data

• Hazardous Substances Data: 4622-04-2(Hazardous Substances Data)

Usage

General Description

2,3-Dicyano-1,4-benzoquinone, also known as DCBQ, is a chemical compound with the molecular formula C8H2N2O2. It is a yellow crystalline solid that is commonly used as an electron acceptor in organic electronic materials. DCBQ is a strong oxidizing agent and is primarily used in the production of conducting polymers, which are widely used in electronic devices such as organic light-emitting diodes and solar cells. It has also been studied for its potential applications in organic batteries and molecular electronics. Additionally, DCBQ has been used in the synthesis of various organic compounds and as a reagent in organic chemistry reactions. However, due to its potential health hazards and environmental impact, precautions should be taken when handling and disposing of this compound.

InChI:InChI=1/C8H2N2O2/c9-3-5-6(4-10)8(12)2-1-7(5)11/h1-2H

Upstream product

• 108148-11-4 3,6-Dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with 2,3-dimethylene-bicyclo[2.2.1]heptane 
• 4733-50-0 2,3-dicyano-1,4-hydroquinone 
• 65192-11-2 2,3-Dicyano-4-hydroxy-phenol anion 
• 4217-54-3 9,10-dihydro-10-methylacridine 
• 56133-30-3 1,4-dihydro-1-(4-methoxybenzyl)pyridine-3-carboxamide 
• 69565-22-6 1-(2,4-dichlorobenzyl)-1,4-dihydronicotinamide 
• 7697-37-2 nitric acid 

Downstream Products

• 108148-11-4 3,6-Dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with 2,3-dimethylene-bicyclo[2.2.1]heptane 
• 40886-09-7 5-chloro-2,3-dicyanohydroquinone 
• 13937-86-5 5-chloro-2,3-dicyano-p-benzoquinone 
• 4640-41-9 2,3-dichloro-5,6-dicyanohydroquinone 
• 4593-00-4 3,6-diacetoxy-4,5-dichloro-phthalonitrile 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 1305344-54-0 ethyl 6-cyano-7-hydroxy-1-imino-2-(4-methoxyphenyl)-3-methyl-10-oxo-2-aza-spiro[4.5]deca-3,6,8-triene-4-carboxylate 
• 1305344-50-6 ethyl 6-cyano-7-hydroxy-1-imino-2-(4-tolyl)-3-methyl-10-oxo-2-aza-spiro[4.5]deca-3,6,8-triene-4-carboxylate 
• 1305344-52-8 ethyl 6-cyano-7-hydroxy-1-imino-2-(4-bromophenyl)-3-methyl-10-oxo-2-aza-spiro[4.5]deca-3,6,8-triene-4-carboxylate 
• 74-90-8 hydrogen cyanide 
• 4733-50-0 2,3-dicyano-1,4-hydroquinone 
• 87963-46-0 3-Amino-3-hydroxy-6-oxo-cyclohexa-1,4-diene-1,2-dicarbonitrile 
• 13367-81-2 10-methylacridinium cation 
• 106551-24-0 5-hydroxy-2-(N-methylanilino)benzofuran-6,7-dicarbonitrile 

Relevant articles and documents

A dicyanobenzoquinone based cathode material for rechargeable lithium and sodium ion batteries

Organic quinone materials offer a sustainable approach for electric energy storage, however, their intrinsic electrical insulation and dissolution into the electrolyte during cycling have hampered their wide applications. To tackle these two issues, we have synthesized a novel organic cathode material by anchoring a quinone compound, 2,3-dicyano-p-benzoquinone (DCBQ) with a high redox potential of 3.37 V vs. Li/Li+, onto carbon nanotubes (CNTs) (CNTs-DCBQ) through a facile ''grafting to'' method. The elaborate combination of excellent electron conductivity and large surface area of CNTs and stable and reversible redox reaction of DCBQ enables CNTs-DCBQ to deliver high reversible capacities of 206.9 and 175.8 mA h g-1 at a current density of 10 mA g-1 and also remarkable capacities of 110.2 and 82.1 mA h g-1 at a higher current density of 200 mA g-1 with a capacity retention approaching 100% after 1000 cycles for lithium and sodium ion batteries, respectively.

Sharp difference in the rate of formation and stability of the Diels–Alder reaction adducts with 2,3-dicyano-1,4-benzoquinone and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylic acid

This work reports new studies of the activity and Diels–Alder kinetics of a series of dienophiles: tetracyanoethylene (1), 2,3-dicyano-p-benzoquinone (10), and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylic acid (11). Rate differences are interpreted in terms of the donor–acceptor properties of the reagents. The relative π-acceptor properties of the dienophiles are probed by measuring their interaction energies with a series π-donor solvents: benzene, toluene, o-xylene, and chlorobenzene. The normalized interaction energies of 1, 10, and 11 are found to be 100:64:28. Despite the increased energy of the donor–acceptor interaction, dienophile 10 is 255 times less active in the reaction with 9,10-dimethylanthracene than 11. It is suggested that this is due to the significantly lower energy of π-bond cleavage in bicyclic dienophile 11, compared with monocyclic 10.