2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Base Information

• Chemical Name: 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane
• CAS No.: 29261-33-4
• Molecular Formula: C12F4N4
• Molecular Weight: 276.152
• Hs Code.: 29269090
• European Community (EC) Number: 624-300-1
• DSSTox Substance ID: DTXSID10369837
• Nikkaji Number: J209.026K
• Wikidata: Q72505259
• Mol file: 29261-33-4.mol

Synonyms:29261-33-4;2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane;2,2'-(Perfluorocyclohexa-2,5-diene-1,4-diylidene)dimalononitrile;2,3,5,6-Tetrafluorotetracyanoquinodimethane;F4-TCNQ;2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile;C12F4N4;F4TCNQ;TCNQF4;2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane;Tetrafluorotetracyanoquinodimethane;MFCD00042382;Propanedinitrile,2,2'-(2,3,5,6-tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)bis-;2,3,5,6-Tetrafluoro-7,7,8,8-tetracyano-quinodimethane;SCHEMBL24272;YSWG343;DTXSID10369837;AMY18874;BCP18920;AKOS005145732;CS-W010077;SB66542;AS-39315;SY050332;FT-0609419;T1131;A819843;7,7,8,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane;2,3,5,6-Tetrafluoro-7,7,8,8,-tetracyano-quinodimethane;2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane, 97%;(2,3,5,6-Tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)dimalononitrile;2,2'-(2,3,5,6-Tetrafluorocyclohexa-2,5-diene-1,4-diylidene)dipropanedinitrile;Propanedinitrile, 2,2'-(2,3,5,6-tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)bis-;2-[4-(dicyanomethylene)-2,3,5,6-tetrafluoro-cyclohexa-2,5-dien-1-ylidene]propanedinitrile

Chemical Property of 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Chemical Property:

• Appearance/Colour: yellow-greenish or orange-brown powder
• Melting Point: 285-290 °C(lit.)
• Boiling Point: -89.6±40.0 °C(Predicted)
• PSA: 95.16000
• Density: 1.57 g/cm³
• LogP: 0.63872
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: insoluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 276.00590867
• Heavy Atom Count: 20
• Complexity: 697

Purity/Quality:

99% ^*data from raw suppliers

Tetrafluorotetracyanoquinodimethane (purified by sublimation) [Organic Electronic Material] >98.0%(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 36/37/38-20/21/22-23/24/25
• Safety Statements: 22-24/25-36/37/39-26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(#N)C(=C1C(=C(C(=C(C#N)C#N)C(=C1F)F)F)F)C#N
• General Description: 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) is a highly electron-deficient quinoidal compound that serves as a key precursor for synthesizing dianionic salts such as (Pr4N)2TCNQF4 and Li2TCNQF4. These derivatives are significant due to their potential applications in electronics and materials science, as they enable the development of metal- and organic-based functional materials. The controlled synthesis of Li2TCNQF4, achieved for the first time on a large scale, highlights its utility as a versatile intermediate for further chemical modifications. The compound's strong electron-accepting properties make it valuable in redox-active systems and charge-transfer materials.

Technology Process of 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

There total 14 articles about 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2,3,5,6-tetrafluoro-1,4-benzoquinone (527-21-9,777826-79-6) + malononitrile (109-77-3) → 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (29261-33-4)

Guidance literature:

With pyridine; titanium tetrachloride; at 200 ℃; Temperature; Reagent/catalyst;

Reference yield: 90.0%

C24H30F4N4O2Si2 → 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (29261-33-4)

Guidance literature:

With triethylamine; trichlorophosphate; at 60 ℃; for 0.166667h;

Reference yield: 88.75%

C22H26F4N4O2Si2 → 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (29261-33-4)

Guidance literature:

With pyridine; phosphorus tribromide; at 100 ℃;

upstream raw materials:

2,3,5,6-Tetrafluor-1,4-bis(tert.-butyldicyanomethyl)benzol

Hexafluorobenzene

2,3,5,6-tetrafluoro-1,4-benzoquinone

malononitrile

Downstream raw materials:

2-(4-Dicyanomethylene-2,3,5,6-tetrafluoro-cyclohexa-2,5-dienylidene)-malononitrile; compound with [2,2']bi[[1,3]dithiolylidene]

N-(phenylmethyl)acetamide

benzaldehyde

diphenyldisulfane

Refernces

Synthetic precursors for TCNQF₄^2a- compounds: Synthesis, characterization, and electrochemical studies of (Pr ₄N)₂TCNQF₄ and Li₂TCNQF₄

10.1021/jo301403v

The study focuses on the synthesis, characterization, and electrochemical investigation of TCNQF4 2? compounds, specifically (Pr4N)2TCNQF4 and Li2TCNQF4. Researchers controlled the reaction stoichiometry and conditions to synthesize both LiTCNQF4 and Li2TCNQF4, with the latter being a significant achievement as it represents the first large-scale chemical synthesis of Li2TCNQF4. The chemicals used in the study included LiI, TCNQF4, acetonitrile, Pr4NBr, and various solvents such as diethyl ether, methanol, and acetone. These chemicals served to react and form the desired TCNQF4 2? salts, which were then characterized using UV?vis, FT-IR, Raman, and NMR spectroscopy, as well as high-resolution electrospray ionization mass spectrometry and electrochemistry. The synthesized compounds are valuable precursors for the synthesis of derivatives of the dianions and can be used to create metal and organic-based materials with potential applications in electronics and materials science.