3138-23-6

Basic information

• Product Name: (3,4-dichlorobenzylidene)propanedinitrile
• Synonyms: (3,4-Dichlorobenzylidene)malononitrile; propanedinitrile, 2-[(3,4-dichlorophenyl)methylene]-
• CAS NO: 3138-23-6
• Molecular Formula: C₁₀H₄Cl₂N₂
• Molecular Weight: 223.0582
• Mol File: 3138-23-6.mol

Chemical Properties

• Boiling Point: 375.5°C at 760 mmHg
• Flash Point: 170.7°C
• Density: 1.417g/cm³
• Vapor Pressure: 7.74E-06mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: (3,4-dichlorobenzylidene)propanedinitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3,4-dichlorobenzylidene)propanedinitrile(3138-23-6)
• EPA Substance Registry System: (3,4-dichlorobenzylidene)propanedinitrile(3138-23-6)

Safety Data

• Hazardous Substances Data: 3138-23-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(3,4-dichlorobenzylidene)propanedinitrile is used as a precursor in the synthesis of various chemicals, contributing to the development of new compounds and materials.
Used in Research Laboratories:
In research settings, (3,4-dichlorobenzylidene)propanedinitrile is employed for its distinctive chemical properties, aiding in the advancement of scientific knowledge and understanding of chemical reactions and processes.
Used in Pharmaceutical Industry:
(3,4-dichlorobenzylidene)propanedinitrile is used as an intermediate in the production of pharmaceuticals, playing a crucial role in the development of new drugs and therapies.
Used in Agrochemical Industry:
(3,4-dichlorobenzylidene)propanedinitrile is also utilized as an intermediate in the synthesis of agrochemicals, contributing to the creation of products that protect crops and enhance agricultural productivity.
However, it is important to note that (3,4-dichlorobenzylidene)propanedinitrile is a potent irritant and can cause irritation to the skin, eyes, and respiratory tract upon contact. Moreover, it has been found to be toxic to aquatic organisms. Due to these potential health and environmental hazards, extreme caution should be exercised when working with (3,4-dichlorobenzylidene)propanedinitrile.

Upstream product

• 6287-38-3 3,4-dichlorobenzaldehyde 
• 109-77-3 malononitrile 

Downstream Products

• 5332-67-2 2-(3,4-dichlorophenyl)-1,1,2-tricyanoethane 
• 293759-04-3 2-amino-4-(3,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 
• 725699-99-0 C₁₃H₇Cl₂N₅O 
• 1266549-90-9 2-amino-4-(3,4-dichlorophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile 
• 1028108-04-4 2-amino-4-(3,4-dichlorophenyl)-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile 
• 156835-49-3 2-amino-4-(3,4-dichlorophenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile 

Relevant articles and documents

Engineering cellulose into water soluble poly(protic ionic liquid) electrolytes in the DBU/CO2/DMSO solvent system as an organocatalyst for the Knoevenagel condensation reaction

The facile design and preparation of polyelectrolytes is a frontier topic in the fields of polymer science, energy storage devices and catalysis. Herein, linear water soluble cellulosic poly(protic ionic liquid) (CPIL) electrolytes were facilely and atom economically prepared after the dissolution of cellulose in the newly developed DBU/CO2/DMSO solvent system, followed by the simple addition of succinic anhydride under mild conditions. The DBU not only participated in the dissolution of cellulose as a solvent component, but also acted as an organocatalyst for the acylation reaction of cellulose with succinic anhydride, as well as a cation component in the targeted CPIL electrolytes. The reaction was optimized, and the effect of the reaction conditions on the chemical and physical properties of the CPILs was investigated. And then, as a proof of concept, the CPIL electrolyte aqueous solution was successfully used as the catalytic reaction media for the Knoevenagel condensation reaction. It was found that the reaction was homogeneous at the beginning, and the products could precipitate out from the media with the proceeding of the reaction, thus affording satisfactory filtration yields ranging from 56.7% to 93.8%. The solution properties of the CPIL aqueous solution were primarily investigated towards an in-depth understanding of the catalytic mechanism, by which a synergetic catalytic mechanism of the CPILs was proposed, and the reaction started with a nucleophilic addition reaction, and was then followed by a fast dehydration reaction. Finally, the direct reusability potential of the CPIL aqueous solution after the product filtration was also primarily investigated for the Knoevenagel condensation reaction.

New Pyrano-4H-benzo[g]chromene-5,10-diones with Antiparasitic and Antioxidant Activities

New pyranonaphthoquinone derivatives were synthesized and investigated for their activity against Trypanosoma brucei, Leishmania major, and Toxoplasma gondii parasites. The pentafluorophenyl derivative was efficacious against T. brucei with single digit m

Design, synthesis and biological evaluation of new series of hexahydroquinoline and fused quinoline derivatives as potent inhibitors of wild-type EGFR and mutant EGFR (L858R and T790M)

New series of hexahydroquinoline and fused quinoline derivatives were designed and synthesized. The thirty seven new compounds were screened for in vitro antitumor activity against HepG2, HCT-116 and MCF-7 cancer cells. Results indicated that compounds 2e

1,4,5,6,7,8-Hexahydroquinolines and 5,6,7,8-tetrahydronaphthalenes: A new class of antitumor agents targeting the colchicine binding site of tubulin

New series of 2-amino-1,4,5,6,7,8-hexahydroquinoline-3-carbonitriles 3a,b and 2-amino-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitriles 4a-h were synthesized and evaluated for their antitumor activity. In vitro antitumor screening of the new members again

Synthesis and anticholinesterase activity of novel non-hepatotoxic naphthyridine-11-amine derivatives

Abstract: In the present study, 14 novel naphthyridine-11-amine derivatives were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 12-(4-Fluorophenyl)-1,2,3,4,7,8,9,10-octahydrodibenz

Phosphahelicenes in asymmetric organocatalysis: [3+2] cyclizations of γ-substituted allenes and electron-poor olefins

The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene- or alkylidenemalononitriles and γ-substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses of up to 97 %.

A PEG bridged tertiary amine functionalized ionic liquid exhibiting thermoregulated reversible biphasic behavior with cyclohexane/isopropanol: Synthesis and application in Knoevenagel condensation

A novel poly(ethylene glycol) bridged tertiary amine functionalized ionic liquid PEG800-DPIL(Cl) was synthesized. It can form a temperature driven reversible biphasic system with cyclohexane/isopropanol mixed solvent. This biphasic system was applied in Knoevenagel condensation up to 99%. PEG 800-DPIL(Cl) could be simply recovered and recycled for several runs.

Isocyanide-based multicomponent reactions: Catalyst-free stereoselective construction of polycyclic spiroindolines

A novel catalyst-free one-pot tandem reaction for the stereoselective construction of polycyclic spiroindolines was developed. This method offers a straightforward access to structurally diverse polycyclic spiroindoline derivatives in high yields (up to 90%) with excellent levels of diastereoselectivity.

A highly efficient protocol for the regio- and stereo-selective synthesis of spiro pyrrolidine and pyrrolizidine derivatives by multicomponent reaction

A series of novel spiro[acenaphthylene-1,2′-pyrrolidine] (4), spiro[acenaphthylene-1,2′-pyrrolizidine] (7), and spiro[indoline-3, 2′-pyrrolidine] derivatives (9) containing cyano group were successfully synthesized via a three-component 1,3-dipolar cycloaddition reaction of acenaphthenequinone or isatin, sarcosine or proline, and Knoevenagel adducts in refluxing aqueous methanol. In this intermolecular three-component combinatorial process it is amazing that three stereogenic centers with one spiro carbon are controlled very well. The structure and relative stereo-chemistry of cycloadducts were carried out by single crystal X-ray diffraction, as well as by the help of 1H, 13C, and HMBC spectroscopy.

Design and an efficient synthesis of natural product-based cyclopenta[b]pyran derivatives with potential bioactivity

A series of 4-aryl-cyclopenta[b]pyran derivatives, designed based on natural product scaffold, were synthesized efficiently via multi-component reaction under solvent-free and catalyst-free conditions. This chemistry provides a new compound library with potential activity for biomedical screening.