2860-54-0

Usage

Uses

Used in Organic Synthesis:
(2,4,6-Cycloheptatriene-1-ylidene)malononitrile is used as a building block in organic synthesis for the creation of various compounds due to its strong electron acceptor properties and ability to participate in addition reactions with nucleophiles such as alkoxides and amines.
Used in Dye Production:
In the dye industry, (2,4,6-Cycloheptatriene-1-ylidene)malononitrile is used as a key intermediate for the production of dyes, leveraging its reactive nature and capacity to form stable complexes.
Used in Pharmaceutical Development:
(2,4,6-Cycloheptatriene-1-ylidene)malononitrile is utilized as a component in the development of pharmaceuticals, taking advantage of its reactivity and potential to form new medicinal compounds.
Used in Agricultural Chemicals:
In agriculture, (2,4,6-Cycloheptatriene-1-ylidene)malononitrile is used in the production of agricultural chemicals, contributing to the development of effective pest control and crop protection agents.
Used in Materials Science:
(2,4,6-Cycloheptatriene-1-ylidene)malononitrile is used as a potent ligand for transition metal complexes in materials science, where it is being explored for its potential to enhance the properties of various materials.
Used in Catalysis Research:
In the field of catalysis, (2,4,6-Cycloheptatriene-1-ylidene)malononitrile is employed as a ligand in the study and development of new catalytic systems, aiming to improve reaction efficiency and selectivity.

InChI:InChI=1/C10H6N2/c11-7-10(8-12)9-5-3-1-2-4-6-9/h1-6H

Upstream product

• 1885-22-9 bromomalononitrile 
• 27081-10-3 cycloheptatrienylium tetrafluoroborate 
• 63718-44-5 7-(Dicyanomethylene)norbornadiene 
• 27081-10-3 tropylium tetrafluoroborate 

Downstream Products

• 141665-70-5 2-((1R,2R,6S,7R)-3-Benzhydrylidene-tricyclo[5.3.2.0^2,6]dodeca-4,9,11-trien-8-ylidene)-malononitrile 
• 141665-69-2 (3aS,3bR,9aS)-3-Benzhydrylidene-3,3a,3b,9a-tetrahydro-cyclopenta[a]azulene-9,9-dicarbonitrile 
• 141665-71-6 2-((1R,2R,6R,7R)-5-Benzhydrylidene-tricyclo[5.3.2.0^2,6]dodeca-3,9,11-trien-8-ylidene)-malononitrile 
• 77959-21-8 2-(6,12-Diphenyl-benzo[4,5]imidazo[1,2-a]cyclohepta[d]pyridin-11-ylidene)-malononitrile 
• 31646-02-3 Cyclohepta-2,4,6-trienylidene-(2,3-diphenyl-cycloprop-2-enyl)-acetonitrile 

Relevant academic research and scientific papers

Synthetic and mechanistic studies of metal-free transfer hydrogenations applying polarized olefins as hydrogen acceptors and amine borane adducts as hydrogen donors

Metal-free transfer hydrogenation of polarized olefins (RR′ CCEE′: R, R′ = H or organyl, E, E′ = CN or CO2Me) using amine borane adducts RR′NH-BH3 (R = R′ = H, AB; R = Me, R′ = H, MAB; R = tBu, R′ = H, tBAB; R = R′ = Me, DMAB) as hydrogen donors, were studied by means of in situ NMR spectroscopy. Deuterium kinetic isotope effects and the traced hydroboration intermediate revealed that the double H transfer process occurred regio-specifically in two steps with hydride before proton transfer characteristics. Studies on substituent effects and Hammett correlation indicated that the rate determining step of the HN transfer is in agreement with a concerted transition state. The very reactive intermediate [NH2BH2] generated from AB was trapped by addition of cyclohexene into the reaction mixture forming Cy2BNH2. The final product borazine (BHNH)3 is assumed to be formed by dehydrocoupling of [NH2BH2] or its solvent stabilized derivative [NH2BH2]-(solvent), rather than by dehydrogenation of cyclotriborazane (BH2NH 2)3 which is the trimerization product of [NH 2BH2].

Synthesis of 5- and 7-(dicyanomethylene)-2,3-dihydrocyclohepta-1,4- dithiins, 'push-pull' heptafulvene derivatives. 8,8-Dicyanoheptafulvenes from α-bromomalononitrile and cycloheptatrienylium salt

Treatment of 2,3-dihydro-4aH-cyclohepta-1,4-dithiin with triphenylmethyl tetrafluoroborate followed by condensation with α-promomalononitrile in pyridine afforded 5- and 7-(dicyanomethylene)-2,3-dihydrocyclohepta-1,4- dithiins in good yields. When changing the solvent to acetonitrile, the products obtained were 5- and 6-(2,2-dicyanoethyl)-2,3-dihydro-1,4- benzodithiins. This new method was applicable to the general synthesis of dicyanoheptafulvenes from tropylium salts.

Carbene Reactions, XVIII. Thermal Behaviour of 7-Alkylidenebicycloheptadiene Derivatives

Thermolysis of 7-alkylidenenorbornadienes 2 results in a retro-Diels-Alder cleavage to fulvenes and acetylene.A different mode of cleavage - into benzene and a carbene - is observed with such derivatives of 2 which carry ?- or ?-donor functions at C-8.The dependence of the reaction pathways on the nature of the substituent at C-8 is discussed on the basis of MO-calculations.