75629-62-8

Basic information

• Product Name: (1H-INDOL-3-YLMETHYLENE)MALONONITRILE
• Synonyms: 2-(1H-indol-3-ylmethylidene)propanedinitrile
• CAS NO: 75629-62-8
• Molecular Formula: C₁₂H₇N₃
• Molecular Weight: 193.2
• Mol File: 75629-62-8.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 437.7°C at 760 mmHg
• Flash Point: 142.1°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 7.33E-08mmHg at 25°C
• Refractive Index: 1.737
• CAS DataBase Reference: (1H-INDOL-3-YLMETHYLENE)MALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (1H-INDOL-3-YLMETHYLENE)MALONONITRILE(75629-62-8)
• EPA Substance Registry System: (1H-INDOL-3-YLMETHYLENE)MALONONITRILE(75629-62-8)

Safety Data

• Hazardous Substances Data: 75629-62-8(Hazardous Substances Data)

Usage

General Description

(1H-Indol-3-ylmethylene)malononitrile is a chemical compound with the chemical formula C13H8N2. It is a yellow to orange solid that is insoluble in water. (1H-INDOL-3-YLMETHYLENE)MALONONITRILE is widely used in organic synthesis and pharmaceutical research as a versatile building block for the synthesis of various indole derivatives. It is also known for its potential biological activities and has been studied for its anti-cancer and anti-inflammatory properties. Additionally, it has been utilized in the development of fluorescent materials and dyes for use in electronic and optoelectronic applications. Overall, (1H-Indol-3-ylmethylene)malononitrile has shown potential for a wide range of applications in the fields of chemistry, pharmaceuticals, and materials science.

InChI:InChI=1/C12H7N3/c13-6-9(7-14)5-10-8-15-12-4-2-1-3-11(10)12/h1-5,8,15H

Upstream product

• 109-77-3 malononitrile 
• 700-06-1 indole-3-carbinol 
• 120-72-9 indole 
• 68-12-2 N,N-dimethyl-formamide 
• 65283-32-1 N-(1H-indol-3-ylmethylene)-N-methylmethanaminium chloride 
• 487-89-8 Indole-3-carboxaldehyde 
• 495-69-2 Hippuric Acid 
• 75629-45-7 (Z)-3-(pyrrolidin-1-ylmethylene)-3H-indole 
• 123-06-8 Ethoxymethylenemalononitrile 

Downstream Products

• 193420-82-5 2-(1-benzyl-1H-indol-3-ylmethylidene)malononitrile 
• 959421-63-7 4-(1H-indol-3-ylmethylene)-5-phenyl-2,4-dihydropyrazol-3-one 
• 884259-09-0 4-(1H-indol-3-ylmethylene)-2,5-diphenyl-2,4-dihydropyrazol-3-one 
• 43106-26-9 4-(1H-indol-3-ylmethylene)-5-methyl-2-phenyl-2,4-dihydropyrazol-3-one 
• 31060-64-7 2-((1H-indol-3-yl)methylene)-1H-indene-1,3(2H)-dione 
• 487-89-8 Indole-3-carboxaldehyde 

Relevant articles and documents

Theoretical, electrochemical and computational inspection for anti-corrosion activity of triazepine derivatives on mild steel in HCl medium

The two triazepine derivatives, 2-amino-9-(1H-indol-3-yl)-4-(4-methoxyphenyl)-7-oxo-1,7-dihydropyrido[1,2-b][1,2,4]triazepine-3,8,10-tricarbonitrile [AITT] and ethyl 2-amino-8,10-dicyano-9-(2-hydroxy-3-methoxyphenyl)-4-(4-methoxyphenyl)-7-oxo-1,7-dihydrop

Ammonium chloride catalyzed Knoevenagel condensation in PEG-400 as ecofriendly solvent

A simple and selective green methodology has been successfully developed for Knoevenagel condensation in polyethylene glycol-400 using 10 mol % ammonium chloride as catalyst. The method is applicable to a wide range of aromatic, heteroaromatic and α,β-unsaturated aldehydes. The reactions have been found to be clean and free from the formation of the Michael adduct.

Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.