2972-72-7

Basic information

• Product Name: (3-methoxybenzylidene)propanedinitrile
• Synonyms: (3-Methoxybenzylidene)malononitrile; 2-(3-Methoxybenzylidene)malononitrile; Benzene, 1-methoxy-3-(2,2-dicyanoethenyl)-; Propanedinitrile, [(3-methoxyphenyl)methylene]-; propanedinitrile, 2-[(3-methoxyphenyl)methylene]-
• CAS NO: 2972-72-7
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.194
• Mol File: 2972-72-7.mol
• Article Data: 95

Chemical Properties

• Boiling Point: 340.4°C at 760 mmHg
• Flash Point: 142.8°C
• Density: 1.169g/cm³
• Vapor Pressure: 8.64E-05mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: (3-methoxybenzylidene)propanedinitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3-methoxybenzylidene)propanedinitrile(2972-72-7)
• EPA Substance Registry System: (3-methoxybenzylidene)propanedinitrile(2972-72-7)

Safety Data

• Hazardous Substances Data: 2972-72-7(Hazardous Substances Data)

Usage

General Description

(3-methoxybenzylidene)propanedinitrile, also known as PMPD, is a chemical compound with the molecular formula C11H9N3O. It is a pale yellow crystalline solid that is commonly used as an intermediate in the synthesis of various organic compounds. PMPD is widely used in the production of dyes, pigments, and pharmaceuticals. It is also a common building block in the manufacturing of specialty chemicals and agricultural products. PMPD is known for its high stability and reactivity, making it a versatile and valuable compound in many industrial applications.

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 109-77-3 malononitrile 
• 670-54-2 ethenetetracarbonitrile 
• 6971-51-3 3-methoxybenzyl alcohol 

Downstream Products

• 866735-28-6 3-amino-4-cyano-5-(o-anisyl)benzocoumarin 
• 582306-96-5 4-Amino-6-(3-methoxy-phenyl)-2-phenyl-pyrimidine-5-carbonitrile 
• 328261-41-2 6-amino-4-(3-methoxyphenyl)-1,4-dihydro-3-methylpyrano[2,3-c]-pyrazole-5-carbonitrile 
• 1177698-04-2 1,6-diamino-4-(3-methoxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile 
• 1207158-30-2 4-allyl-2-(3-methoxy-phenyl)-3-phenyl-cyclopent-3-ene-1,1-dicarbonitrile 
• 1379679-72-7 N-[2-chloro-2,2-dicyano-1-(3-methoxyphenyl)ethyl]pyrrolidine-2,5-dione 
• 1379679-64-7 N-[2-bromo-2,2-dicyano-1-(3-methoxyphenyl)ethyl]pyrrolidine-2,5-dione 
• 1291067-37-2 2-((1H-indol-3-yl)(3-methoxyphenyl)methyl)malononitrile 

Relevant articles and documents

A multifunctional triazine-based nanoporous polymer as a versatile organocatalyst for CO2 utilization and C-C bond formation

A triazine-based nanoporous multifunctional polymer with a SABET of 304 m2 g-1 has shown versatile catalytic activity in the conversion of CO2 to cyclic carbonates at 4 bar with almost 100% yield and selectivity, and in the conversion of CO2 to methanol and methane electrochemically. Additionally, it also catalyzes C-C bond formation via the Knoevenagel reaction.

Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4-amino-5-cyanopyrimidine) derivatives

A series of bis(4-amino-5-cyano-pyrimidines) was synthesized and evaluated as dual inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). To further explore the multifunctional properties of the new derivatives, their antioxidant and antibacterial activities were also tested. The results showed that most of these compounds could effectively inhibit AChE and BChE. Particularly, compound 7c exhibited the best AChE inhibitory activity (IC50 = 5.72 ± 1.53 μM), whereas compound 7h was identified as the most potent BChE inhibitor (IC50 = 12.19 ± 0.57 μM). Molecular modeling study revealed that compounds 7c, 7f, and 7b showed a higher inhibitory activity than that of galantamine against both AChE and BChE. Anticholinesterase activity of compounds 7h, 7b, and 7c was significant in vitro and in silico for both enzymes, since these compounds have hydrophobic rings (Br-phenyl, dimethyl, and methoxyphenyl), which bind very well in both sites. In addition to cholinesterase inhibitory activities, these compounds showed different levels of antioxidant activities. Indeed, in the superoxide–dimethyl sulfoxide alkaline assay, compound 7j showed very high inhibition (IC50 = 0.37 ± 0.28 μM). Also, compound 7l exhibited strong and good antibacterial activity against Staphylococcus epidermidis and Staphylococcus aureus, respectively. Taking into account the results of biological evaluation, further modifications will be designed to increase potency on different targets. In this study, the obtained results can be a new starting point for further development of multifunctional agents for the treatment of Alzheimer's disease.

Successive oxidation-condensation reactions using a multifunctional gold-supported nanocomposite (Au/MgCe-HDO)

The application of gold-supported nanocomposites is useful in clinical diagnostics because of their ability to provide bio-compatible and sensitive detection systems. A gold-supported magnesium hydroxide and cerium oxide nanocomposite framework (Au/MgCe-HDO) was synthesized and characterized via XRD, XPS, SEM, DLS, TEM, and TGA techniques. The nanocomposite was used as a selective catalyst for the aerobic oxidation of alcohols under mild reaction conditions followed by successive condensation reactions, like Knoevenagel and Claisen-Schmidt condensation. Substituted benzyl alcohols were converted into the corresponding carbonyl compounds in the presence of the Au/MgCe-HDO nanocomposite with O2 gas and toluene as a solvent. We observed that, upon the addition of malononitrile/ethyl cyanoacetate/acetophenone to the catalyst in the aerobic oxidation reaction, the reaction proceeds to produce the corresponding desired condensation product with up to 95% yield.

Introduction of succinimide as a green and sustainable organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b] pyran derivatives

Aim and Objective: In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives