10432-39-0

Basic information

• Product Name: (1-phenylpropylidene)propanedinitrile
• Synonyms: (1-Phenylpropylidene)malononitrile; propanedinitrile, 2-(1-phenylpropylidene)-
• CAS NO: 10432-39-0
• Molecular Formula: C₁₂H₁₀N₂
• Molecular Weight: 182.2212
• Mol File: 10432-39-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 302.1°C at 760 mmHg
• Flash Point: 134.2°C
• Density: 1.072g/cm³
• Vapor Pressure: 0.00101mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: (1-phenylpropylidene)propanedinitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (1-phenylpropylidene)propanedinitrile(10432-39-0)
• EPA Substance Registry System: (1-phenylpropylidene)propanedinitrile(10432-39-0)

Safety Data

• Hazardous Substances Data: 10432-39-0(Hazardous Substances Data)

Usage

General Description

(1-phenylpropylidene)propanedinitrile, also known as α-phenylcinnamylidene malononitrile or CS gas, is a chemical compound commonly used in riot control and crowd control agents. It is a potent irritant and can cause severe eye and respiratory irritation, as well as skin irritation and respiratory distress. The compound is typically disseminated as an aerosol or powder and can cause immediate discomfort and incapacitation in exposed individuals. It is important to handle this chemical with caution and use protective equipment when working with it to avoid adverse health effects.

Upstream product

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

Downstream Products

• 10432-48-1 3-Ethyl-3-phenyl-cyclopropane-1,1,2,2-tetracarbonitrile 
• 1846-21-5 2-(1-phenylpropyl)malononitrile 
• 65996-15-8 4-Dimethylamino-3-methyl-2-phenyl-1,3-butadien-1,1-dicarbonitril 
• 63615-38-3 1,1-Dichloro-2,2-dicyano-3-ethyl-3-phenylcyclopropan 
• 78032-73-2 (S)-3-Ethyl-3-phenyl-oxirane-2,2-dicarboxylic acid dimethyl ester 
• 78032-73-2 (R)-3-Ethyl-3-phenyl-oxirane-2,2-dicarboxylic acid dimethyl ester 
• 1248412-52-3 2-chloro-7-imino-10-methyl-6a-nitro-6,9-diphenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 
• 1248412-53-4 6-(4-chlorophenyl)-7-imino-10-methyl-6a-nitro-9-phenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 
• 1248412-54-5 7-imino-10-methyl-6a-nitro-9-phenyl-6-p-tolyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 
• 1438276-61-9 (6S,6aR,10aR)-7-amino-2-chloro-10-methyl-6a-nitro-6,9-diphenyl-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile 
• 1438276-79-9 (6S,6aR,10aR)-2-chloro-7-imino-10-methyl-6a-nitro-6,9-diphenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 
• 1438276-63-1 (6S,6aR,10aR)-7-amino-2-bromo-10-methyl-6a-nitro-6,9-diphenyl-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile 
• 1438276-80-2 (6S,6aR,10aR)-2-bromo-7-imino-10-methyl-6a-nitro-6,9-diphenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 

Relevant articles and documents

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.

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.

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 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.