1487-82-7

Basic information

• Product Name: 2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE
• Synonyms: 2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE;Dimethyltetracyanoquinodimethane;2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE 97+%;(3,6-Dimethyl-2,5-cyclohexadiene-1,4-diylidene)bis(malononitrile);2,2'-(2,5-Dimethyl-2,5-cyclohexanediene-1,4-diylidene)bis(propanedinitrile);2,5-Dimethyl-2,5-cyclohexadiene-1,4-diylidenebis(malononitrile);2,5-Dimethyltetracyanoquinodimethane;7,7,8,8-Tetracyano-2,5-dimethyl-p-quinodimethane
• CAS NO: 1487-82-7
• Molecular Formula: C₁₄H₈N₄
• Molecular Weight: 232.24
• Product Categories: Acceptors (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials;TCNQ Derivatives
• Mol File: 1487-82-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE(1487-82-7)
• EPA Substance Registry System: 2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE(1487-82-7)

Safety Data

• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1487-82-7(Hazardous Substances Data)

Usage

General Description

2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE (TCDQ) is an organic compound with a chemical formula of C14H10N4. It is a dark green crystalline solid that is commonly used as an electron acceptor in organic electronic devices and as a reagent in organic synthesis. TCDQ is known for its strong electron-accepting properties and is often used in combination with electron-donating compounds to create charge-transfer complexes. It has been extensively studied for its potential applications in organic solar cells, organic field-effect transistors, and organic light-emitting diodes. Additionally, TCDQ has also been investigated for its potential use as a catalyst and as a precursor in the synthesis of new organic materials.

Upstream product

• 1518-17-8 bis(dicyanomethylene)-2,5-dimethylcyclohexane 
• 1134-68-5 2,5-dimethyl-1,4-phenylenediacetonitrile 
• 6298-72-2 2,5-bis(chloromethyl)-p-xylene 
• 96812-95-2 2-(4-Dicyanomethyl-2,5-dimethyl-phenyl)-malononitrile 
• 2082-66-8 2-chlorobenzylthiocyanate 
• 99779-61-0 2-[4-(Dicyano-trimethylsilanyloxy-methyl)-2,5-dimethyl-phenyl]-2-trimethylsilanyloxy-malononitrile 
• 21004-07-9 Dicyano-[4-(dicyano-methoxycarbonyl-methyl)-2,5-dimethyl-phenyl]-acetic acid methyl ester 

Downstream Products

• 60665-14-7 2-(4-Dicyanomethylene-2,5-dimethyl-cyclohexa-2,5-dienylidene)-malononitrile; compound with [2,2']bi[[1,3]dithiolylidene] 
• 111139-82-3 {(C₆(CH₃)6)2Fe}⁽²⁺⁾*2{(CN)2CC₆H₂(CH₃)2C(CN)2}^(1-)*(CN)2CC₆H₂(CH₃)2C(CN)2*2CH₃NO₂={(C₆(CH₃)6)2Fe}{C₁₄H₈N₄}3*2CH₃NO₂ 
• 128517-28-2 3,4-Dimethyl-1,2,5,6-tetraselena-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-2,5-dimethyl-cyclohexa-2,5-dienylidene)-malononitrile 
• 128517-27-1 3,4-Dimethyl-1,2,5,6-tetrathia-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-2,5-dimethyl-cyclohexa-2,5-dienylidene)-malononitrile 
• 128517-29-3 3,4-Dimethyl-1,2,5,6-tetratellura-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-2,5-dimethyl-cyclohexa-2,5-dienylidene)-malononitrile 

Relevant articles and documents

Average Structure of Bis(oxamide oximato)nickel(II) * Dimethyl-tetracyanoquinodimethane, a "Charge Transfer" Compound with Mixed Stacks and Variable Paramagnetism

The average unit cell of the methanol solvate *C14H8N4*2CH3OH, Mr = 589.22 is triclinic, P, a = 8.539(3), b = 8.937(3), c = 9.418(3) Angstroem, α = 103.39(3), β = 100.12(2), γ = 105.39(2) deg, V = 652,2 Angstroem3, Z = 1, dc = 1.50 g cm-3, final Rw=0.050 for 1580 observed independent reflections.Satellite reflections hint at a modulation of the structure in the ac plane.Mixed stacks of alternating and mainly neutral metal complex and Me2tcnq molecules are formed.Crystals grown with electrochemical reduction show a weak activated paramagne tism, those grown without electrochemical support are diamagnetic. - Keywords: Charge Transfer Compound, Mixed Stacks, Modulated Structure

SUBSTITUTED 7,7',8,8'-TETRACYANOQUINODIMETHANES. I. METHODS OF SYNTHESIS OF SUBSTITUTED 7,7',8,8'-TETRACYANOQUINODIMETHANES

The synthesis of 2-methyl-, 2,5-dimethyl-, and 2-isopropyl-7,7'-8,8'-tetracyanoquinodimethanes was realized from 2-methyl-, 2,5-dimethyl-, and 2-isopropyl-1,4-cyclohexanediones.These cyclic diketones are obtained with good yields by the Birch reduction of 2-chloromethyl-, 2,5-dichloromethyl-, and 2-isopropyl-1,4-dimethoxybenzenes.