14778-29-1

Usage

Physical properties

White crystalline solid, Melting point of 158-160°C, Soluble in polar organic solvents

Reactivity

Highly reactive

Toxicity

Toxic

Uses

Building block in organic synthesis for creating a variety of compounds, used to produce pharmaceuticals, dyes, and other specialty chemicals

Handling precautions

Handle with caution due to toxic nature and potential for harmful effects on health and environment.

InChI:InChI=1/C6H2N4/c7-1-5(2-8)6(3-9)4-10/h5-6H

Upstream product

• 670-54-2 ethenetetracarbonitrile 
• 98138-11-5 1,1,2,2-tetracyano-ethanesulfonic acid 
• 123439-12-3 4-amino[2.2]paracyclophane 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 107-56-2 O,O-diisopropyl hydrogen phosphorodithioate 
• 77820-60-1 1-(4-isoindolin-2-yl-phenyl)-ethanone 
• 73357-41-2 2-(2-Chlorphenyl)-isoindolin 
• 73357-40-1 2-(3-methoxyphenyl)-2,3-dihydro-1H-isoindole 
• 1885-22-9 bromomalononitrile 
• 109-77-3 malononitrile 
• 65032-86-2 1-benzyl-1,4,5,6-tetrahydropyridine-3-carboxamide 
• 613-94-5 benzoic acid hydrazide 
• 5055-39-0 indole-2-carbohydrazide 
• 1452-63-7 picolinic acid hydrazide 

Downstream Products

• 110059-07-9 1,4-diamino-2,3-dicyano-1,4-bis(phenylthio)butadiene 
• 109511-58-2 U₀₁₂₆ 
• 88745-03-3 5-Amino-1-(4-chloro-phenyl)-2-phenyl-1,2-dihydro-pyrrole-3,3,4-tricarbonitrile 
• 118373-55-0 C₂₂H₁₁ClN₄O₂ 
• 97866-29-0 2,4,6-trioxo-2'-amino-5'-phenyl-3',4',4'-tricyanoperhydropyrimidine-5-spiro-1'-(2'-cyclopentene) 
• 118373-50-5 (5S,6S)-9-Amino-6-(4-chloro-phenyl)-4-methyl-1-oxo-2-oxa-3-aza-spiro[4.4]nona-3,8-diene-7,7,8-tricarbonitrile 
• 93971-41-6 1-Ethyl-3-imino-5-phenyl-2-oxa-bicyclo[2.2.1]heptane-4,7,7-tricarbonitrile 
• 118644-92-1 3-Imino-1-methyl-5-phenyl-2-oxa-bicyclo[2.2.1]heptane-4,7,7-tricarbonitrile 
• 97841-67-3 3-methyl-5-oxo-2'-amino-5'-phenyl-3',4',4'-tricyanoisoxazoline-4-spiro-1'-(2'-cyclopentene) 
• 97841-67-3 (5S,6S)-9-Amino-4-methyl-1-oxo-6-phenyl-2-oxa-3-aza-spiro[4.4]nona-3,8-diene-7,7,8-tricarbonitrile 
• 97841-67-3 3-methyl-5-oxo-2'-amino-5'-phenyl-3',4',4'-tricyano-oxazoline-4-spiro-1'-cyclopent-2'-ene 
• 93971-43-8 5-Acetyl-6-methyl-1,3-dioxo-4-phenyl-2,3,4,7-tetrahydro-1H-isoindole-3a,7a-dicarbonitrile 
• 165056-53-1 2,5-di(2-chlorophenyl)-3,3,4,4-tetracyanopyrrolidine 
• 142683-05-4 2,5-di(2-methoxyphenyl)-3,3,4,4-tetracyanopyrrolidine 

Relevant academic research and scientific papers

Novel [2.2]paracyclophane derivatives via charge-transfer complexation

The transannular electronic interactions in [2.2]paracyclophanes affect the selectivity of the tricyanovinylation reaction with tetracyanoethylene (TCNE). In addition to the normal N-tricyanovinyl product, 4-amino[2.2]paracyclophane reacts with TCNE to give oxaziridine derivatives. In the case of reaction with 4-N-methylamino[2.2]paracyclophane, the unusual N-tricyanovinylated product as well as 4-(N-carbonitrile-N-methyl)amino[2.2]paracyclophane was isolated. The reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with 4-amino[2.2]paracyclophane results in formation of 2-cyano-3-(4-[2.2]paracyclophanyl)amino-5,6-dichloro-1,4-benzoquinone.

New reaction of ethenetetracarbonitrile with N-arylisoindolines

N-Arylisoindolines 1a-i react with ethenetetracarbonitrile 2 in aerated benzene by formation of [3-(2-aryl-3-dicyanomethylene-2,3-dihydro-1H-isoindol-1-ylidene)-2-aryl-2, 3-dihydro-1H-isoindol-1-ylidene]propanedinitriles 8a-i (20-36%), N-aryl-3-dicyanomethylene-isoindol-2-ones 9a-i (15-21%) and N-arylphthalimides 10a-i (4-9%) as well as 1,1,2,2-tetracyanoethane 11 (35-55%). The structure of 8d has been unambiguously confirmed by a single crystal X-ray structure analysis. A rationale for the formation of products 8-11 is presented.

The interaction of 1,1,2-tricarbamoyl-2-cyanoethane with alkyl vinyl ketones - A new approach to [3.3.3]propellanes

Single-stage synthesis of 3,7-diacyl-2,6-diamino-9,11-dioxo-10- aza[3,3,3]propella-2,6-dienes from 1,1,2-tricarbamoyl-2-cyanoethane and alkyl vinyl ketones, is reported.

A three-valued photoelectrochemical logic device realising accept anything and consensus operations

A new application of a hybrid material exhibiting the photoelectrochemical photocurrent switching (peps) effect in a three-valued logic device is reported. In contrast to other similar peps-based systems, the one described here is capable of performing basic ternary logic operations: gullibility and consensus. This journal is

Reactions of substituted carbohydrazides with electron-poor olefins

Substituted carbohydrazides 1a-e reacted with ethenetetracarbonitrile (2) in dimethylformamide with formation of diacylhydrazines 4a-e and 5-amino-1-substiuted pyrazole-3,3,4-tricarbonitriles 5a-e. On the other hand, 1a-c reacted with diethyl (E)-2,3-dicy

Chemical reactivity of 3-hydrazino-5,6-diphenyl-1,2,4-triazine towards π-acceptors activated carbonitriles

Behaviour of 3-hydrazino-5,6-diphenyl-1,2,4-triazine 1 as electron donor towards different electron acceptors activated carbonitriles has been investigated and a novel fused heterocyclic system and 2,3-disubstituted 1,2,4-triazines have been obtained. Compound 1 reacts with 1,2-dicyanobenzene as π-acceptor in DMF to form benzencarboximidamide 16, while reaction of 1 with a-bromomalononitrile 17 in boiling DMF affords compound 18. On the other hand, compound 1 reacts with tetracyanoethane 23 in DMF to yield compound 24. The route of reaction in DMF indicates that charge-transfer complexation is the key intermediate to obtain new heterocyclic systems. Structures of the products are established by MS, IR, UV-Vis, CHN and 1H NMR spectral data.

EVIDENCE FOR A SINGLE ELECTRON TRANSFER ACTIVATION IN THE HYDRIDE TRANSFER FROM AN NADH MODEL COMPOUND TO TETRACYANOETHYLENE

New evidence for a stepwise mechanism which requires a single electron transfer activation in the hydride transfer from an NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH), to tetracyanoethylene (TCNE) has been presented based on the effects of pyridine on the stoichiometry of the overall reaction, the rate constant, and the kinetic isotope effect.