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Tetracyanoethylene

Base Information Edit
  • Chemical Name:Tetracyanoethylene
  • CAS No.:670-54-2
  • Deprecated CAS:51778-96-2,56875-27-5
  • Molecular Formula:C6N4
  • Molecular Weight:128.093
  • Hs Code.:29269095
  • European Community (EC) Number:211-578-0
  • NSC Number:24833
  • UNII:C592309ECU
  • DSSTox Substance ID:DTXSID7049425
  • Nikkaji Number:J7.085H,J2.225.846J
  • Wikipedia:Tetracyanoethylene
  • Wikidata:Q413864
  • ChEMBL ID:CHEMBL3188794
  • Mol file:670-54-2.mol
Tetracyanoethylene

Synonyms:Ethenetetracarbonitrile(6CI,8CI,9CI); 1,1,2,2-Tetracyanoethene; 1,1,2,2-Tetracyanoethylene; Ethene,tetracyano-; Ethylenetetracarbonitrile; NSC 24833; TCNE; Tetracyanoethene;Tetracyanoethylene; D2,2'-Bimalononitrile

Suppliers and Price of Tetracyanoethylene
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • AHH
  • Tetracyanoethylene 98%
  • 1000g
  • $ 1280.00
  • AK Scientific
  • Tetracyanoethylene
  • 25g
  • $ 128.00
  • Alfa Aesar
  • Tetracyanoethylene 98%
  • 1g
  • $ 25.00
  • Alfa Aesar
  • Tetracyanoethylene 98%
  • 5g
  • $ 70.50
  • American Custom Chemicals Corporation
  • TETRACYANOETHYLENE 95.00%
  • 1G
  • $ 128.10
  • Chem-Impex
  • Tetracyanoethylene,98%(GC) 98%(GC)
  • 25G
  • $ 128.80
  • Chem-Impex
  • Tetracyanoethylene,≥98%(GC)Hazmat ≥98%(GC)
  • 5G
  • $ 40.77
  • Chem-Impex
  • Tetracyanoethylene,98%(GC) 98%(GC)
  • 1G
  • $ 11.20
  • Chem-Impex
  • Tetracyanoethylene,98%(GC) 98%(GC)
  • 100G
  • $ 448.00
  • Matrix Scientific
  • Ethene-1,1,2,2-tetracarbonitrile 95+%
  • 100g
  • $ 699.00
Total 19 raw suppliers
Chemical Property of Tetracyanoethylene Edit
Chemical Property:
  • Appearance/Colour:Beige powder. 
  • Vapor Pressure:0.117mmHg at 25°C 
  • Melting Point:197-199 ºC 
  • Refractive Index:1.5600 
  • Boiling Point:223 ºC 
  • Flash Point:223ºC 
  • PSA:95.16000 
  • Density:1,348 g/cm3 
  • LogP:0.37732 
  • Storage Temp.:2-8°C 
  • Sensitive.:Moisture Sensitive 
  • Water Solubility.:hydrolyzes 
  • XLogP3:-0.2
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:4
  • Rotatable Bond Count:0
  • Exact Mass:128.012296017
  • Heavy Atom Count:10
  • Complexity:289
Purity/Quality:

98% *data from raw suppliers

Tetracyanoethylene 98% *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes:T+ 
  • Statements: 20/21-28-23/24 
  • Safety Statements: 28-36/37-45-28A-22-1 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Nitrogen Compounds -> Nitriles
  • Canonical SMILES:C(#N)C(=C(C#N)C#N)C#N
  • General Description Tetracyanoethylene (TCNE) is a strong organic electron acceptor widely used in the synthesis of push-pull chromophores for optoelectronic applications, such as OLEDs and solar cells, due to its high electron affinity. It serves as a key reactant in cycloaddition reactions to form compounds with intense charge-transfer properties and comparable reduction potentials to benchmark acceptors like TCNQ. Additionally, TCNE is utilized in the synthesis of nonlinear optical (NLO) polymers, contributing to enhanced thermal stability and dipole alignment for electro-optic devices. Its versatility extends to heterocyclic chemistry, where it facilitates the efficient synthesis of pharmacologically relevant compounds, such as 4-arylaminoisoquinazoline-2-carbonitriles. Furthermore, TCNE reacts with ferrocenylethynyl complexes to form derivatives with unique electrochemical properties, highlighting its role in organometallic chemistry.
Technology Process of Tetracyanoethylene

There total 132 articles about Tetracyanoethylene 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:
Guidance literature:
With sulfur dichloride; In acetonitrile; at -40°C;
DOI:10.1021/ja00878a017
Guidance literature:
With selenium(IV) oxide; In toluene; at 100 ℃; for 1.25h;
DOI:10.1134/S1070428017030253
Guidance literature:
In 1,1,2,2-tetrachloroethylene; chloroform; refluxing of soln. of educts (8 h), distn. of solvent, warming of residue at 100-150°C and 20-40 Torr (2 h); sublimation, recrystn. (twice) from chlorobenzene;
DOI:10.1021/ja01544a051
Refernces Edit

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

10.1039/b714731g

The research focuses on the development of new strong organic acceptors through the [2 + 2] cycloaddition of tetracyanoethene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) to donor-substituted cyanoalkynes, followed by retro-electrocyclisation. The purpose of this study was to synthesize potent organic acceptors that could rival the electron uptake propensity of benchmark compounds TCNE and TCNQ, which are highly demanded in the fabrication of optical light-emitting diodes (OLEDs) and solar cells. The researchers successfully prepared donor-substituted 1,1,2,4,4-pentacyanobuta-1,3-dienes (PCBDs) and a cyclohexa-2,5-diene-1,4-diylidene-expanded derivative, which exhibited intense bathochromically-shifted intramolecular charge-transfer bands and underwent their first one-electron reductions at potentials similar to those reported for TCNE and TCNQ. The study concluded that these new push-pull chromophores not only matched the electron-accepting power of TCNE and TCNQ but also showed promise for optoelectronic applications.

Synthesis and nonlinear optical properties of novel polyester containing tricyanovinylthiophene with enhanced thermal stability of second harmonic generation

10.1080/15421400902950170

This research aimed to synthesize and characterize a novel Y-type polyester containing 1-(2,4-dioxyethoxy)phenyl-2-{5-(1,2,2-tricyanovinyl)-2-thiophenyl)}ethenyl groups as nonlinear optical (NLO) chromophores. The purpose was to develop a polymer that combines the advantages of both main-chain and side-chain NLO polymers, such as stable dipole alignment and good solubility, for potential applications in electro-optic devices. The key chemicals used included monomer 5, terephthaloyl chloride, and tetracyanoethylene. The resulting polymer, designated as polymer 7, exhibited thermal stability up to 300°C with a glass transition temperature (Tg) of around 134°C. Its second harmonic generation (SHG) coefficient was measured at 6.74 × 10?? esu, and it demonstrated high thermal stability of dipole alignment, with no significant SHG decay observed below 135°C. The study concluded that this new type of NLO polyester has potential for use in NLO device applications due to its enhanced thermal stability and solubility.

A general synthesis of 4-arylaminoquinazoline-2-carbonitriles

10.1515/znb-2009-0715

The research focuses on the one-step synthesis of 4-arylaminoisoquinazoline-2-carbonitriles, a class of heterocyclic compounds with significant pharmacological importance. The study aims to improve the yield of products obtained from the reaction of 2-aminobenzonitrile and various aniline derivatives, and to synthesize 4-arylaminoisoquinazoline-2-carbonitrile derivatives that could not be obtained by conventional methods. The reactants used include 2-aminoarylbenzimidamides and tetracyanoethylene (TCNE), with the synthesis carried out in ethyl acetate at room temperature for 4 to 6 hours. The synthesized compounds were characterized using various spectroscopic methods such as IR and NMR spectroscopy, and the structure of one of the benzimidamide compounds was confirmed by single crystal X-ray diffraction. The experiments resulted in moderate to good yields of the target compounds, demonstrating a simple and efficient method for synthesizing these heterocyclic compounds.

Syntheses, structures, some reactions, and electrochemical oxidation of ferrocenylethynyl complexes of iron, ruthenium, and osmium

10.1021/om050483l

The research focuses on the synthesis, characterization, and electrochemical properties of various ferrocenylethynyl complexes containing iron (Fe), ruthenium (Ru), and osmium (Os). The study explores the attachment of ferrocenylethynyl and ferrocene-1,1′-bis(ethynyl) groups to metal centers such as M(PP)Cp′, where M represents Fe, Ru, or Os, and PP denotes different phosphine ligands. The researchers synthesized these complexes using various chemical reactions, including the use of tetracyanoethene (tcne) to form tetracyanobuta-1,3-dienyl or η3-allylic derivatives, and the addition of Me+ to create vinylidene derivatives. The molecular structures of 14 of these complexes were determined by crystallographic methods. The study investigates the electronic communication between the redox-active metal centers through the ferrocene nucleus and provides insights into the electrochemical behavior of these complexes. Key chemicals involved in the research include ferrocene derivatives, ruthenium and osmium compounds, phosphine ligands such as dppe (1,2-bis(diphenylphosphino)ethane), and tetracyanoethene.

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