13166-10-4

Usage

Uses

Used in Pharmaceutical Industry:
ISOPROPYLIDENEMALONONITRILE is used as a key intermediate in the synthesis of pyridopyrimidine derivatives, which possess a range of biological activities. These derivatives are valuable for the development of new drugs with antibacterial, antiviral, and anticancer properties, contributing to the advancement of treatments for various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, ISOPROPYLIDENEMALONONITRILE serves as a vital component in the creation of compounds with pesticidal and herbicidal properties. Its role in the synthesis of these agrochemicals helps in developing effective solutions for crop protection and management of pests and weeds.
Used as a Nucleophilic Reagent in Organic Synthesis:
ISOPROPYLIDENEMALONONITRILE is utilized as a nucleophilic reagent in various organic reactions due to the presence of the cyano group. This functionality allows it to participate in a wide array of chemical transformations, leading to the production of diverse functionalized products that can be applied across different industries, including the synthesis of specialty chemicals and materials.

InChI:InChI=1/C6H6N2/c1-5(2)6(3-7)4-8/h1-2H3

Upstream product

• 110-89-4 piperidine 
• 64-19-7 acetic acid 
• 67-64-1 acetone 
• 109-77-3 malononitrile 
• 64-17-5 ethanol 
• 917-58-8 potassium ethoxide 
• 917-54-4 methyllithium 
• 93102-10-4 dicyano-1,1 propadiene 
• 78386-09-1 1,1-dicyano-2,4-dimethyl-4-phenylpent-1-ene 
• 80982-69-0 dicyanomethylene-O,O-diethyl phosphorane 
• 107-95-9 3-amino propanoic acid 

Downstream Products

• 1203-13-0 2-cyano-3-methyl-3-phenylbutyronitrile 
• 30481-45-9 2-amino-4,6,6-trimethylcyclohexa-2,4-diene-1,1,3-tricarbonitrile 
• 16738-89-9 2-Butyl-2-methyl-cyclopropane-1,1-dicarbonitrile 
• 13017-67-9 3,3-dimethylcyclopropane-1,1,2,2-tetracarbonitrile 
• 4210-60-0 t-butylmalonodinitrile 
• 102354-00-7 2-[(E)-3-(Ethyl-phenyl-amino)-1-methyl-allylidene]-malononitrile 
• 102354-04-1 2-[(E)-3-(Cyclohexyl-methyl-amino)-1-methyl-allylidene]-malononitrile 
• 102354-01-8 2-[(E)-3-(Butyl-phenyl-amino)-1-methyl-allylidene]-malononitrile 
• 102354-03-0 2-[(E)-3-(Benzyl-methyl-amino)-1-methyl-allylidene]-malononitrile 
• 221049-69-0 2-amino-4,4,7,7-tetramethyl-5-oxo-3-cyano-5,6,7,8-tetrahydro-4H-benzopyran 
• 67-64-1 acetone 
• 109-77-3 malononitrile 
• 475115-47-0 2-amino-9-(2-chlorophenyl)-3-cyano-4-methyl-7-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]thieno[3,2-b]pyridine 
• 74528-83-9 4,6,6-trimethyl-2-oxo-cyclohex-3-ene-1,1,3-tricarbonitrile 

Relevant academic research and scientific papers

Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine

2-Chloro-3-amino-4-picoline (CAPIC) is a strategic building block for the preparation of nevirapine, a widely-prescribed nonnucleosidic reverse transcriptase inhibitor for the treatment of HIV-infected patients. A continuous synthesis to the bromo derivative of a CAPIC intermediate, 2-bromo-4- methylnicotinonitrile, that terminates in a dead-end crystallization is described. The route uses inexpensive, acyclic commodity-based raw materials and has the potential to enable lower cost production of nevirapine as well as other value added structures that contain complex pyridines. The route terminates in a batch crystallization yielding high purity CAPIC. This outcome is expected to facilitate regulatory implementation of the overall process.

MICROWAVE SPECTRUM OF 1,1'-DIMETHYL-22'-DICYANOETHYLENE

The microwave spectra of 1,1'-dimethyl-2,2'-dicyanoethylyne and 1,1'-dimethyl-2,2'-dicyanoethylene-d6 have been recorded in the frequency region 18-40 GHz.The measured ground state lines have been fitted to a semi-rigid rotor model.From the resulting six moments of inertia some structural information has been obtained.

Molybdenum hexacarbonyl-catalyzed condensation of malononitrile with ketones and aldehydes

Molybdenum hexacarbonyl activated with pyridine or morpholine catalyzes the condensation of malononitrile with ketones and aldehydes at 140 C, which leads to alkylidenemalononitriles in 75-100% yield.

Ylidenemalononitrile enamines as fluorescent "turn-on" indicators for primary amines

Ylidenemalononitrile enamines undergo rapid amine exchange followed by a cyclization with primary amines to yield fluorescent products with emission intensities as high as 900 times greater than the starting materials. After identifying the fluorescent species by X-ray crystallography, we demonstrate that the rate of amine exchange is substrate dependent and that by simple structural variation the fluorescence can be tuned over the entire visible spectrum. We further demonstrate their potential application in biomolecule labeling.

Preparation of mesoporous carbon nitride materials using urea and formaldehyde as precursors and catalytic application as solid bases

A series of mesoporous carbon nitride materials have been fabricated using inexpensive and eco-friendly urea and formaldehyde as precursors and mesocellular silica foam (MCF) as a template through a nanocasting approach. Several techniques, including XRD, TEM, elemental analysis, FT-IR, XPS, and CO2-TPD have been applied to characterize the physicochemical properties of the mesoCN materials, and the results show that the materials possess high surface areas (331–355?m2?g?1), relatively concentrated pore size of ca. 6?nm, and abundant and multiple nitrogen-containing species. As heterogeneous base catalysts, mesoCN materials demonstrate high catalytic activity and selectivity in both Knoevenagel condensation and transesterification reactions.

Synthesis of two-dimensional mesoporous carbon nitride under different carbonization temperatures and investigation of its catalytic properties in Knoevenagel condensations

A two-dimensional mesoporous carbon nitride (MCN-1) material with tunable surface area, pore volume and nitrogen content has been synthesized by using carbon tetrachloride and ethylenediamine as precursors and SBA-15 as a template. The effect of the carbonization temperature on the textural properties, N content and the types of nitrogen species of the MCN-1 samples was also investigated by several characterization techniques. The results reveal that the higher temperature favors the formation of porous structure during the thermal condensation process. In addition, the nitrogen content and the surface N/C ratio in the samples monotonically decrease with the increase of carbonization temperature. The catalytic activity of MCN-1-T is not only related to its surface nitrogen content but also dependent on the structural diversities of the surface nitrogen species. The MCN-1 sample synthesized at 400 °C shows the higher catalytic activity and stability for Knoevenagel condensations. This journal is

Observations of tetrel bonding between sp3-carbon and THF

We report the direct observation of tetrel bonding interactions between sp3-carbons of the supramolecular synthon 3,3-dimethyl-tetracyanocyclopropane (1) and tetrahydrofuran in the gas and crystalline phase. The intermolecular contact is establishedvias-holes and is driven mainly by electrostatic forces. The complex manifests distinct binding geometries when captured in the crystalline phase and in the gas phase. We elucidate these binding trends using complementary gas phase quantum chemical calculations and find a total binding energy of -11.2 kcal mol-1for the adduct. Our observations pave the way for novel strategies to engineer sp3-C centred non-covalent bonding schemes for supramolecular chemistry.

A bis(heptafulvenyl)-dicyanoethylene thermoswitch with two sites for ring closure

Suitably functionalized vinylheptafulvenes (VHFs) act as thermoswitches undergoing ring closure to the corresponding dihydroazulenes (DHAs). Here we present the synthesis of a new such thermoswitch incorporating two heptafulvene rings on a dicyanoethylene

Liquid-phase Knoevenagel reactions over modified basic microporous titanosilicate ETS-10

Al- and Ga-incorporated ETS-10, designated as ETAlS-10 and ETGaS-10, respectively, were synthesized by using P25 titania as a Ti source. The isomorphous substitution of Al and Ga for framework Si at the (4Si) environment was confirmed by 29Si M

Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds

An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.