3111-60-2

Usage

Uses

Used in Organic Synthesis:
2-[1-(4-CHLOROPHENYL)ETHYLIDENE]MALONONITRILE is used as a reagent for the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block in the creation of complex molecules.
Used in Pharmaceutical Development:
Due to its potential biological activity, 2-[1-(4-CHLOROPHENYL)ETHYLIDENE]MALONONITRILE is studied for its potential use in the development of pharmaceuticals. It may act as an inhibitor for certain enzymes, which could be beneficial in treating specific medical conditions.
Used in Agrochemical Development:
2-[1-(4-CHLOROPHENYL)ETHYLIDENE]MALONONITRILE is also being studied for its potential use in the development of agrochemicals. Its ability to inhibit certain enzymes could be useful in creating effective pesticides or herbicides.
Used in Research:
2-[1-(4-CHLOROPHENYL)ETHYLIDENE]MALONONITRILE is utilized in research settings to study its properties and potential applications. Understanding its reactivity and interactions with other molecules can lead to new discoveries and innovations in various fields.
Note: Due to the toxic and reactive nature of 2-[1-(4-CHLOROPHENYL)ETHYLIDENE]MALONONITRILE, proper handling and safety precautions are necessary when working with 2-[1-(4-CHLOROPHENYL)ETHYLIDENE]MALONONITRILE.

InChI:InChI=1/C11H7ClN2/c1-8(10(6-13)7-14)9-2-4-11(12)5-3-9/h2-5H,1H3

Upstream product

• 99-91-2 para-chloroacetophenone 
• 109-77-3 malononitrile 
• 115998-04-4 2-[2-Bromo-1-(4-chloro-phenyl)-ethylidene]-malononitrile 
• 108-98-5 thiophenol 
• 98-86-2 acetophenone 

Downstream Products

• 21448-26-0 3-(4-Chlorphenyl)-2.2-dicyan-buttersaeure-ethylester 
• 23250-07-9 1-Phenyl-3-(4-chlor-phenyl)-2.2-dicyan-butanon-⁽¹⁾ 
• 89507-37-9 [6-Amino-4-(4-chloro-phenyl)-5-cyano-thiopyran-(2E)-ylidene]-cyano-acetic acid ethyl ester 
• 79111-74-3 4-(4-Chlorphenyl)-2-methylthio-penta-1,4-dien-1,1,5,5-tetracarbonitril 
• 72503-65-2 (E)-5-(4-Chloro-phenyl)-2,6,6-tricyano-3-methylsulfanyl-hexa-2,5-dienoic acid ethyl ester 
• 77198-34-6 2-Amino-4-(4-chloro-phenyl)-6-phenyl-cyclohexa-2,4-diene-1,1,3-tricarbonitrile 
• 104581-09-1 5'-amino-4-chloro-4''-methyl-1,1':3',1''-terphenyl-4',6'-dicarbonitrile 
• 144738-21-6 2-{1-(4-Chloro-phenyl)-2-[(4-chloro-phenyl)-hydrazono]-ethylidene}-malononitrile 
• 80067-23-8 2-{1-(4-Chloro-phenyl)-2-[5-phenyl-[1,2]dithiol-(3Z)-ylidene]-ethylidene}-malononitrile 
• 106000-61-7 2-Amino-4,6-bis-(4-chloro-phenyl)-6-methyl-cyclohexa-2,4-diene-1,1,3-tricarbonitrile 
• 131534-29-7 2-amino-4-(p-chlorophenyl)-4-methyl-6-phenyl-4H-pyran-3,5-dicarbonitrile 
• 143644-48-8 6-amino-4-(4-chlorophenyl)-1,2-dihydro-2-oxo-1-phenylpyridine-5-carbonitrile 
• 143644-49-9 5-(4-chlorophenyl)-2,7-dithioxo-3,8-diphenyl-1,2,3,7,8-pentahydropyrido<2,3-d>pyrimidine-4-imine 
• 127844-80-8 <2-Phenylhydrazono-1-(4-chlorophenyl)ethylidene>malononitrile 

Relevant academic research and scientific papers

Exploitation of dual character of CN moiety in the synthesis of uniquely decorated 3 H-pyrroles: A rare observation

This is the first report of an innovative, one-pot, organocatalyzed, multicomponent synthesis of 3H-pyrroles from ketones, thiols, and malononitrile in ecofriendly solvent water. The approach to 3H-pyrroles presented herein offers, for the first time, an unprecedented coupling which leads to the construction of the nitrogen containing ring without starting from any amine moiety. In this context, cyanide-based multicomponent reactions involving the dual nature of the CN moiety has blossomed in an unprecedented way.

Synthesis, in vivo anti-inflammatory, COX-1/COX-2 and 5-LOX inhibitory activities of new 2,3,4-trisubstituted thiophene derivatives

New series of thiophene derivatives were synthesized and evaluated for their in vivo anti-inflammatory activity using carrageenan-induced paw edema model. The most active in vivo anti-inflammatory compounds 5b, 11b, 14c, 18c, 19c and 20d were further evaluated for their in vitro COX-1/COX-2 and 5-LOX inhibitory activities. The in vitro assay results revealed that the N-(4-(4-chlorophenyl)-3-cyanothiophen-2-yl)-2-morpholinoacetamide (5b) possesses the highest selectivity toward COX-2 (IC50 = 5.45 μM) with selectivity index value of 8.37 compared to celecoxib with COX-2 selectivity index value of 15.44. In addition, it showed acceptable 5-LOX inhibitory activity (IC50 = 4.33 μM) compared to NDGA (IC50 = 2.46 μM). Molecular modeling study was conducted to study the postulated binding of compound 5b into the active site of COX-2 and 5-LOX, and it revealed that 5b binds similarly to celecoxib and NDGA, respectively. Overall, the morpholinoacetamide-thiophene hybrid 5b could serve as a promising lead for further development of new potent anti-inflammatory agents that act as dual COX-2/5-LOX inhibitors.

A [5 + 1] annulation strategy for the synthesis of multifunctional biaryls and: P -teraryls from 1,6-Michael acceptor ketene dithioacetals

A new type of ketene dithioacetal, 2-(3,3-bis-methylsulfanyl-1-arylallylidene)malononitriles containing 1,4 and 1,6-Michael acceptors, were synthesized to study their reactivity for the synthesis of a new molecular entity. We report a [5 + 1] annulation s

Transition metal free synthesis of multifunctional thiomethylated-benzenes from aryl/heteroaryl/cyclopropyl methyl ketones

A base-promoted strategic synthesis of various functionalized thiomethylated-benzenes has been established from aryl/heteroaryl/cyclopropyl methyl ketone. We can directly access the thiomethylated-benzene nucleus embedded with diverse functional group by

"on Water" Direct Catalytic Vinylogous Aldol Reaction of Silyl Glyoxylates

The unique reactivity of water in the direct catalytic vinylogous aldol reaction of silyl glyoxylates is reported. With the hydrogen-bonding networks from water, the unfavorable homogeneous reactions in organic solvents were severely suppressed, and the "

Synthesis of Functionalized Bicyclic Compounds Based on 2-(1-Arylethylidene)malononitriles

New tetrahydroisoquinoline-5,7-dicarbonitrile derivatives have been synthesized by piperazine hydrate-catalyzed reaction of acetoacetanilide with 2-(1-arylethylidene)malononitriles (Knoevenagel condensation products of acetophenones and malononitrile) in

Phosphine-catalyzed domino reaction: A novel sequential [2+3] and [3+2] annulation reaction of γ-substituent allenoates to construct bicyclic[3, 3, 0]octene derivatives

We have successfully developed a novel and efficient phosphine-catalyzed sequential [2+3] and [3+2] annulation reaction of γ-substituent allenoates to construct bicyclic[3, 3, 0]octene derivatives. The protocol uses readily available γ-substituent allenoa

Synthesis and evaluation of 4-anilinoquinazoline bioisosteres as potential anti-breast cancer agents

Based on one of the four major categories of scaffold hopping theory namely hetrocycle replacements, a series of 5-arylthieno[2,3-d]pyrimidines had been prepared and evaluated as anti-breast cancer agents. Optimization by combination of different pharmacophores with the thienopyrimidine scaffold led to discovery of biologically active compounds.

Pseudo-five-component domino strategy for the combinatorial library synthesis of [1,6] naphthyridines - An on-water approach

This work features the base-promoted on-water synthesis of [1,6]-naphthyridines from methyl ketones, malononitrile and phenols or thiols. The reaction conditions were carefully tuned to drive the product selectivity from 3H-pyrroles to [1,6]-naphthyridines. The advantages of this method lie in its simplicity, cost effectiveness, and environmental friendliness, representing a new effort toward the on-water synthesis of [1,6]-naphthyridines without starting from a nitrogen-containing heterocycle and highlighting the versatility of the nitrile functional group.

[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