6673-15-0

Basic information

• Product Name: 2-[4-(dimethylamino)phenyl]ethene-1,1,2-tricarbonitrile
• Synonyms: 2-Cyano-3-(4-dimethylamino-phenyl)-but-2-enedinitrile; p-Tricyanovinyl-N,N-dimethylaniline
• CAS NO: 6673-15-0
• Molecular Formula: C₁₃H₁₀N₄
• Molecular Weight: 222.2453
• Mol File: 6673-15-0.mol

Chemical Properties

• Boiling Point: 375.3°C at 760 mmHg
• Flash Point: 164.5°C
• Density: 1.203g/cm³
• Vapor Pressure: 7.88E-06mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 2-[4-(dimethylamino)phenyl]ethene-1,1,2-tricarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[4-(dimethylamino)phenyl]ethene-1,1,2-tricarbonitrile(6673-15-0)
• EPA Substance Registry System: 2-[4-(dimethylamino)phenyl]ethene-1,1,2-tricarbonitrile(6673-15-0)

Safety Data

• Hazardous Substances Data: 6673-15-0(Hazardous Substances Data)

Usage

General Description

2-[4-(dimethylamino)phenyl]ethene-1,1,2-tricarbonitrile is a chemical compound that is also known as DMAPTEDTCN. It is an organic compound with a highly specialized structure. 2-[4-(dimethylamino)phenyl]ethene-1,1,2-tricarbonitrile is a tricarbonitrile derivative of ethene and contains a dimethylamino group attached to a phenyl ring. DMAPTEDTCN is often used in organic synthesis and materials science as a building block for more complex molecules. Its unique structure and reactive properties make it useful in the development of various pharmaceuticals, dyes, and other functional materials.

Upstream product

• 89745-73-3 tricyanovinyl bromide 
• 121-69-7 N,N-dimethyl-aniline 
• 2826-28-0 p-(N-dimethylamino benzylidene) malononitrile 
• 3189-44-4 2,2,1-tricyano-1-hydroxy-ethylene, tetramethyl-ammonium salt 
• 109-77-3 malononitrile 
• 205651-05-4 ethyl pentacyanocyclopropanecarboxylate 
• 139952-06-0 Hexacyanocyclopropane 
• 35462-54-5 N,N-Dimethylaniline hydroiodide 
• 3189-43-3 tetracyanoethylene oxide 
• 40591-10-4 p-N,N-dimethylaminobenzoyl nitrile 
• 55260-60-1 10-(1,1,2,2-Tetracyanoaethyl)anthron 
• 33342-62-0 chloroethene tricarbonitrile 
• 670-54-2 ethenetetracarbonitrile 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 100517-62-2 2-[amino-(4-dimethylaminophenyl)methylene]malononitrile 
• 97443-78-2 (4-dimethylamino-3-nitro-phenyl)-ethenetricarbonitrile 
• 21859-65-4 1-(2.2-Dimethyl-hydrazino)-1-(4-dimethylamino-phenyl)-2.2-dicyan-ethylen 
• 173259-95-5 5-amino-3-(4-(dimethylamino)phenyl)-2,3-dihydro-1-phenyl-1H-pyrazole-4-carbonitrile 
• 1326216-08-3 2-[(4-dimethylaminophenyl)(methylamino)methylene]malononitrile 
• 1326216-10-7 2-[(4-dimethylaminophenyl)(thiomorpholin-4-yl)methylene]malononitrile 
• 70819-00-0 2-[(4-dimethylaminophenyl)(morpholin-4-yl)methylene]malononitrile 
• 70819-01-1 2-[(4-dimethylaminophenyl)piperidin-1-yl-methylene]malononitrile 
• 1326216-09-4 2-[(4-dimethylaminophenyl)pyrrolidin-1-yl-methylene]malononitrile 
• 173260-06-5 dimethyl 4-amino-3-(p-dimethylaminophenyl)-1-phenylpyrazolo[3,4-b]pyridine-5,6-dicarboxylate 
• 72558-73-7 2,4,7-Trinitro-fluoren-9-one; compound with 2-cyano-3-(4-dimethylamino-phenyl)-but-2-enedinitrile 
• 15994-03-3 1-(O,O-Diethylphosphono)-1-(p-dimethylaminophenyl)-1,2,2-tricyanethan 
• 102082-00-8 2-(4-dimethylamino-phenyl)-4,5-dimethyl-cyclohex-4-ene-1,1,2-tricarbonitrile 
• 100882-16-4 2-[dimethylamino-(4-dimethylaminophenyl)methylene]malononitrile 

Relevant articles and documents

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.

Photophysical properties of arylcarbonitrile derivatives: Synthesis, absorption and emission spectra, and quantum chemical studies

A new series of aromatic cyanovinyl compounds were synthesized via one-pot reactions of tri- or tetracyanoethylenes with nucleophilic reagents. The ground-state geometries and UV-vis absorption spectra of the compounds were computationally analyzed by means of density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations, respectively. None of the compounds were fluorescent in solution, but some showed intense emission in the solid state. The first excited singlet states (S1) potential energy surfaces (PESs) were explored using complete active space SCF (CASSCF) calculations for the compounds in order to elucidate nonradiative decay mechanism that takes into account the involvement of conical intersections (CI).

Reactions of 2′-oxo-1′,2′-dihydrospiro[cyclopropane-1, 3′-indole]-2,2,3,3-tetracarbonitriles with nucleophiles

2′-Oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole] -2,2,3,3-tetracarbonitriles reacted with oxygencentered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the presence of base catalyst, and the products, 2-amino-4,4-dialkoxy-2′-oxo-1′, 2′-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1, 5-dicarbonitriles, were converted into the corresponding 2-imino-2′,4- dioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1,5-dicarbonitriles and 2,2′,4-trioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1, 5-dicarbonitriles by the action of acetic and sulfuric acids, respectively. The reactions with ketone oximes occurred in the absence of a catalyst, yielding 2-amino-4,4-bis(alkylideneaminooxy)-2′-oxo-1′,2′- dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1, 5-dicarbonitriles. The reactions with thiols, aliphatic amines, and anilines were accompanied by opening of the three-membered ring. In the reactions with triphenylphosphine and thiols 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene) malononitrile was obtained, while morpholine and N,N-dimethylaniline gave rise, respectively, to 3,3-diaryl-and 3,3-dimorpholino-1H-indol-2(3H)-ones and tri- and dicyanoethylene derivatives.

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.

Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates

Triselenium dicyanide is formed by the interaction of malononitrile and selenium dioxide in dimethylsulfoxide or dimethylformamide. Addition of aromatic amines, indoles and some active methylene compounds to this reaction mixture gives the corresponding s

Reaction of ethyl pentacyanocyclopropanecarboxylate with amines

Reaction of ethyl pentacyanocyclopropanecarboxylate with aliphatic amines yields the corresponding pentacyano-2-propen-1-ides, and in reaction with aromatic amines depending on the structure of the original amine arise N,N-dialkyl-4-(tricyanovinyl)anilines and bis(N,N-dialkylaminophenyl)malononitriles or ethyl 2-arylamino-1,2-dicyanoethene-1-carboxylates.

Reaction of polycyanocyclopropanes with amine hydroiodides

Reactions of ethyl 1,2,2,3,3-pentacyanocyclopropanecarboxylate, l,3-dioxoindan-2-spirocyclopropane-2′,2′,3′,3′- tetracarbonitrile, 2,4,6-trioxoperhydropyrimidine-5-spirocyclopropane-2′,2′,3′, 3′-tetracarbonitrile, and 4,4-dimethyl-2,6-dioxocyclohexanespirocyclopropane-2′,2′,3′, 3′-tetracarbonitrile with amine hydroiodides yield, depending on the structure of the initial cyclopropane, 1-ethoxycarbonyl-1,2,3,3-tetracyanopropenides, ethyl 3-arylamino-2,3-dicyanoacrylates, N,N-dialkyl-4-(tricyanovinyl)anilines, (4-dimethylaminophenyl)(1,3-dioxoindan-2-yl)malononitrile, (l,3-dioxoindan-2-yl)(4-tolylamino)malononitrile, 5-[aryl(dicyano)methyl]perhydropyrimidine-2,4,6-triones, and 2-amino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4Hchromene-3,4,4-tricarbonitrile.

Hexacyanocyclopropane. III. Reaction of Hexacyanocyclopropane with Aromatic Amines

Reaction of hexacyanocyclopropane with aromatic amines yields N- and C-tricyanovinylanilines. A mechanism of this reaction is proposed on the basis of stoichiometric ratios in the reactions of hexacyanocyclopropane and tetracyanoethylene oxide with aromatic amines.

Hexacyanocyclopropane. II. Reaction of Hexacyanocyclopropane with Aliphatic and Aromatic Amine Hydroiodides

Reaction of hexacyanocyclopropane with aliphatic amine hydroiodides gives corresponding pentacyano-2-propen-1-ides and cyanogen iodide, whereas with aromatic amine hydroiodides unsubstituted and ring-substituted N-(tricyanovinyl)anilines or N,N-dialkyl-4-(tricyanovinyl)anilines, malononitrile, and iodine are formed.

Cyanovinylheteroaromatics for Organic Nonlinear Optics

Effects of various substituents including chromophores on the second harmonic generation (SHG) of cyanovinylheteroaromatics were examined.The molecular polarizability was calculated by the PPP MO method to correlate SHG responsiveness with chemical structures. 3-indole 8b exhibited good SHG efficiency (PE = 25U).The X-ray analysis of 8b showed that the crystals belong to novel and the most favorable P1 space group.