10432-39-0

Usage

Uses

Used in Riot Control:
(1-phenylpropylidene)propanedinitrile is used as a riot control agent for its ability to cause immediate discomfort and incapacitation in exposed individuals. Its effectiveness in this application stems from its potent irritant properties, which lead to severe eye and respiratory irritation, as well as skin irritation and respiratory distress.
Used in Crowd Control:
In crowd control situations, (1-phenylpropylidene)propanedinitrile is utilized as a crowd control agent to manage and disperse large gatherings. (1-phenylpropylidene)propanedinitrile is typically disseminated as an aerosol or powder, allowing for wide-area coverage and ensuring that it reaches a significant number of individuals in the crowd, thereby facilitating crowd management and maintaining public safety.
It is crucial to handle (1-phenylpropylidene)propanedinitrile with caution and to use appropriate protective equipment when working with it to prevent adverse health effects on those in its vicinity.

Upstream product

• 333-27-7 methyl trifluoromethanesulfonate 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 
• 93-55-0 1-phenyl-propan-1-one 
• 109-77-3 malononitrile 

Downstream Products

• 63615-38-3 1,1-Dichloro-2,2-dicyano-3-ethyl-3-phenylcyclopropan 
• 112754-03-7 2(1,1-Dicyan-2-phenyl-but-2-en-1-yl)-3(4,4-dicyan-3-phenyl-but-3-en-2-yl)bernsteinsaeuredimethylester 
• 163563-64-2 2-Chloro-4-phenyl-3-pyridinecarbonitrile 
• 116263-58-2 3-Methyl-2-phenyl-1-azulencarbonitril 
• 116263-51-5 3-Methyl-2-phenyl-8aH-azulene-1,1-dicarbonitrile 
• 1180845-14-0 C₂₄H₂₂N₂O₂ 
• 65996-21-6 2-bromo-5-methyl-4-phenylnicotinonitrile 

Relevant academic research and scientific papers

Solvent-free condensations of ketones with malononitrile catalysed by methanesulfonic acid/morpholine system

The preparation of ylidenemalononitriles via Knoevenagel condensations of ketones with malononitrile under solvent-free conditions is described. Good yields and short reaction time are the features observed with methanesulfonic acid (MSA)/morpholine used as the catalyst. The wide applicability of the protocol is shown by the fact that not only unconjugated, but also aryl-alkyl ketones gave satisfactory yields.

Enantioselective direct vinylogous Michael addition reaction catalyzed by organic molecules

Chiral 2-azanorbornyl-3-methanol is used as an organocatalyst for the highly enantioselective direct vinylogous Michael addition reaction of vinyl malononitriles to α,β-unsaturated aldehydes. In many cases, the products can be obtained in almost optically

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.

Synthesis method of methylene malononitrile compounds

The invention discloses a synthesis method of methylene malononitrile compounds. According to the method, in the air atmosphere, a ketone compound and malononitrile are taken as raw materials, Ru/C istaken as a catalyst, the raw materials and the catalyst

INHIBITORS OF THE PD-1/PD-L1 PROTEIN/PROTEIN INTERACTION

The present invention provides novel compounds of formula (I) that are useful as inhibitors of the PD-1/PD-L1 protein/protein interaction.

Synthesis of methyl 3-azidothieno[2,3-b]pyridine-2-carboxylates and application of the huisgen reaction

The preparation of new substituted methyl 3-azidothieno[2,3-b]pyridine carboxylates by azotization of methyl 3-aminothieno[2,3-b]pyridine and subsequent treatment with sodium azide is described. Via Huisgen's 1,3-dipolar cycloaddition between substituted alkynes and the prepared azides, methyl 1,2,3-triazolo-thieno[2,3-b]pyridine carboxylates have been obtained.

Synthesis and bioactivity of novel amino-pyrazolopyridines

Here we describe the synthesis and biological activity of novel amino-pyrazolopyridines with anti-NF-κB and pro-apoptotic potential. α-Methylene ketones were used as a starting point for synthesis of amino-pyrazolopyridine 3. The alkylidene malononitriles 1 were obtained by the Knoevenagel reaction of ketones with malononitriles. Vilsmeier-Haack reaction allowed direct access to 2-chloro-3-cyanopyridines 2. Those products, by refluxing with hydrazine hydrate, allowed cyclization to amino-pyrazolopyridines 3a-g, which were not previously described in the literature. Bioactivity results indicated that amino-pyrazolopyridines 3a, 3b and 3g induced apoptotic cell death in K562 cancer cells with an IC50 of 36.5 ± 3.9 μM, 27.6 ± 4.5 μM and 35.0 ± 2.3 μM, respectively, after 72 h. In addition, compounds 3a, 3b and 3g exerted NF-κB inhibition activity with an IC50 of 4.7 ± 1.6 μM, 6.9 ± 1.9 μM and 39.8 ± 3.9 μM, respectively, after 8 h in K562 cells activated with TNFα. Compounds 3b and 3g showed interesting differential toxicity as viability of peripheral blood mononuclear cells (PBMCs) from healthy donors remained largely unaffected by this treatment.

Improved synthesis of mono- and disubstituted 2-halonicotinonitriles from alkylidene malononitriles

Pyridines with 2,3,4 and/or 5 substitution remain challenging to prepare. Existing strategies to form multisubstituted 2-halonicotinonitriles via enamines suffer from dimerization of the starting alkylidene malononitriles resulting in low yields. Through alteration of reaction conditions, a new high yielding method into enamines was realized by condensing DMF-DMA and alkylidene malononitriles in the presence of substoichiometric acetic anhydride. Cyclization of the resulting enamines under Pinner conditions provided 2-halonicotinonitriles in high overall yields.

[5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: A synthetic route to multi-substituted 2-aminopyridines

A facile and efficient synthetic route to multi-substituted 2-aminopyridines has been developed via a formal [5C + 1N] annulation of readily available 2,4-pentadienenitriles with hydroxylamine (NH2OH) under very mild conditions, which involves

Facile metal free regioselective transfer hydrogenation of polarized olefins with ammonia borane

Transfer hydrogenation of polarized olefins bearing strongly electron-withdrawing groups on one side of the double bond was achieved with ammonia borane under mild conditions without using a catalyst. Mechanistic studies proved the character of the direct H transfers proceeding stepwise with a unique hydroboration intermediate and hydride before proton transfer.