24789-99-9

Basic information

• Product Name: [4-(diethylamino)phenyl]ethylenetricarbonitrile
• Synonyms: [4-(diethylamino)phenyl]ethylenetricarbonitrile;1-[4-(Diethylamino)phenyl]-1,2,2-ethenetricarbonitrile;2-[4-(Diethylamino)phenyl]-1,1,2-ethenetricarbonitrile;2-Cyano-3-[4-(diethylamino)phenyl]-2-butenedinitrile;4-(Tricyanovinyl)-N,N-diethylaniline;N,N-Diethyl-4-(tricyanovinyl)aniline;α-Cyano-4-(diethylamino)benzylidenemalononitrile;(4-(Diethylamino)phenyl)ethenetricarbonitrile
• CAS NO: 24789-99-9
• Molecular Formula: C₁₅H₁₄N₄
• Molecular Weight: 252.31434
• EINECS: 246-460-8
• Mol File: 24789-99-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 400.4°Cat760mmHg
• Flash Point: 172.3°C
• Appearance: /
• Density: 1.149g/cm³
• Vapor Pressure: 1.28E-06mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: [4-(diethylamino)phenyl]ethylenetricarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: [4-(diethylamino)phenyl]ethylenetricarbonitrile(24789-99-9)
• EPA Substance Registry System: [4-(diethylamino)phenyl]ethylenetricarbonitrile(24789-99-9)

Safety Data

• Hazardous Substances Data: 24789-99-9(Hazardous Substances Data)

Usage

Description

[4-(diethylamino)phenyl]ethylenetricarbonitrile, with the chemical formula C20H22N4, is a tricyanovinyl-substituted diphenylamine. It is recognized for its good thermal stability and excellent electron transport properties, making it a promising compound for various technological applications.

Uses

Used in Electronics Industry:
[4-(diethylamino)phenyl]ethylenetricarbonitrile is used as an electron transporting material for organic light-emitting diodes (OLEDs) due to its high electron mobility and efficiency in converting light into electricity.
Used in Photovoltaic Applications:
In the renewable energy sector, [4-(diethylamino)phenyl]ethylenetricarbonitrile is studied for its potential applications in organic photovoltaic devices, as it exhibits high electron mobility and efficiency in converting light into electricity, which can contribute to the development of more efficient solar panels.

InChI:InChI=1/C15H14N4/c1-3-19(4-2)14-7-5-12(6-8-14)15(11-18)13(9-16)10-17/h5-8H,3-4H2,1-2H3

Upstream product

• 670-54-2 ethenetetracarbonitrile 
• 91-66-7 N,N-diethylaniline 
• 3189-44-4 2,2,1-tricyano-1-hydroxy-ethylene, tetramethyl-ammonium salt 
• 205651-05-4 ethyl pentacyanocyclopropanecarboxylate 
• 19452-37-0 N,N-Diethylaniline hydroiodide 
• 139952-06-0 Hexacyanocyclopropane 
• 89745-73-3 tricyanovinyl bromide 
• 33342-62-0 chloroethene tricarbonitrile 

Downstream Products

• 1326216-12-9 2-(dimethylamino[(4-diethylaminophenyl)methylene])malononitrile 
• 1326216-11-8 2-[(4-diethylaminophenyl)(morpholin-4-yl)methylene]malononitrile 

Relevant articles and documents

TRICANOVINYLATION OF PHENOXAZINE AND PHENOTHIAZINE

In the reaction of tricynoethylene (TCE) with phenoxazine in DMF at 100 deg C, in addition to the principal reaction product - viz., 3-(tricynovinyl)phenoxazine - 3-dicyanomethylene-3H-phenoxazine and 3-phenoxazinyl-3-(3H-phenoxazinylene)-cyanomethane are formed in small amounts.The latter two compounds were also obtained from phenoxazine and dibromomalononitrile.Phenothiazine reacts similarly with tetracyanoethylene.A reaction scheme is proposed, and in this scheme the formation of side products is explained by significant electron transfer in the tetracyanoethylene-heterocycle system.For the first time, 1,6 cleavage of HCN was detected, in which (in contrast to the known 1,6 cleavage of HCN from carbon atoms) the hydrogen is split out from the nitrogen atom.

Eco-friendly and recyclable media for rapid synthesis of tricyanovinylated aromatics using biocatalyst and deep eutectic solvent

An efficient and clean synthesis of aromatic tricyanovinyl compounds from nucleophilic reagent and tetracyanoethylene has been achieved using biocatalyst and deep eutectic solvent (DES). Reaction using biocatalyst and DES requires lesser reaction time than conventional method. The advantages of the present method are ambient reaction temperature, easy isolation of the product, higher yield, recyclability of the catalyst, and reactions without use of hazardous, volatile organic solvent. The DES as well as biocatalyst were recycled efficiently without any additional treatment. Synthesized compounds were also studied for UV-vis absorption and show solvatochromism.

An improved method for tricyanovinilation of aromatic amines under ultrasound irradiation

A synthetic method for tricyanovinylation under ultrasound irradiation has been developed for preparation of tricyanovinyl aromatic amines. The method is reliable and can be applied to the synthesis of a variety of tricyanovinyl compounds, with high yields, purity and with short reaction times.