41097-37-4

Usage

Uses

Used in Pharmaceutical Industry:
(1E, 2E)-1,2-bis(4-chlorobenzylidene) hydrazine is used as a precursor in the synthesis of pharmaceuticals for its potential applications in the development of anti-cancer drugs. Its unique structure allows for the creation of novel compounds that can target and combat cancer cells effectively.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (1E, 2E)-1,2-bis(4-chlorobenzylidene) hydrazine serves as a valuable compound for research and development. Its potential antimicrobial and anti-inflammatory properties make it a promising candidate for the creation of new drugs to treat various infections and inflammatory conditions.
Used in Organic Synthesis:
(1E, 2E)-1,2-bis(4-chlorobenzylidene) hydrazine is utilized as a key intermediate in organic synthesis, enabling the production of a wide range of organic compounds with diverse applications. Its versatility as a building block contributes to the advancement of chemical research and the development of new materials and products.

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 104-88-1 4-chlorobenzaldehyde 
• 31061-79-7 benzoic acid (4-chlorobenzylidene)hydrazide 
• 19277-54-4 p-chlorophenyldiazomethane 
• 90701-80-7 N-(o-azidobenzoyl)-p-chlorobenzaldehyd hydrazone 
• 691-38-3 (Z)-4-methyl-2-pentene 
• 110-82-7 cyclohexane 
• 354-58-5 1,1,1-Trichloro-2,2,2-trifluoroethane 
• 52372-80-2 (4-chlorobenzylidene)hydrazine 
• 558-13-4 carbon tetrabromide 
• 76-13-1 1,1,2-Trichloro-1,2,2-trifluoroethane 
• 56-23-5 tetrachloromethane 
• 75-27-4 bromodichloromethane 
• 124-48-1 chlorodibromomethane 

Downstream Products

• 722-32-7 (2-(4-chlorophenyl)methylene)hydrazolyl-1,3-thiazolidin-4-one 
• 904-60-9 4-chloro-benzaldehyde [5-(4-chloro-benzylidene)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 111474-68-1 4,4'-Dichlor-benzaldazin-monoxyd 
• 5406-33-7 4-chlorobenzyl acetate 
• 74-11-3 para-chlorobenzoic acid 
• 61094-67-5 (4-Chlorphenyl)bis(methylthio)methan 
• 104-88-1 4-chlorobenzaldehyde 
• 62441-81-0 2,6-di(4-chlorophenyl)-1,3,5,7-tetraazabicyclo[3.3.0]octane-4,8-dione-3,7-disulfonyl chloride 
• 1166381-83-4 7,14-bis(4-chlorophenyl)-11,11-dimethyl-1,4,10,12-tetraoxadispiro[4.2.5.2]pentadecane-9,13-dione 
• 870080-23-2 3,3-dimethyl-7,11-cis-di(p-chlorophenyl)-2,4-dioxaspiro[5.5]undecane-1,5,9-trione 
• 907169-67-9 3,7-bis(4-chlorophenyl)-tetrahydro-[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithione 
• 1374997-37-1 diethyl [(2E)-2-(4-chlorobenzylidene)hydrazino](4-chlorophenyl)methyl phosphonate 
• 1613288-01-9 C₅₀H₄₄Cl₄N₄O₄P₂ 
• 86212-34-2 (1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine 

Relevant academic research and scientific papers

Effect of the catalyst nature and quantity on catalytic olefination

The study of the catalyst nature effect on the catalytic olefination of 4-chlorobenzaldehyde hydrazone by polyhaloalkanes revealed that the best catalysts for the reaction are copper salts. With polyhaloalkanes more active than CCl4, like CBrs

Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines

Herein, an efficient and simple catalytic method for the selective and partial reduction of aldazines using ruthenium catalyst [Ru(p-cymene)Cl2]2 (1) has been accomplished. Under mild conditions, aldazines undergo the addition of pinacolborane in the presence of a ruthenium catalyst, which delivered N-boryl-N-benzyl hydrazone products. Notably, the reaction is highly selective, and results in exclusive mono-hydroboration and desymmetrization of symmetrical aldazines. Mechanistic studies indicate the involvement of in situ formed intermediate [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1a) in this selective hydroboration.

Non-Pincer-Type Arene Ru(II) Catalysts for the Direct Synthesis of Azines from Alcohols and Hydrazine under Aerobic Conditions

We report a tandem approach to synthesize symmetrical azines from alcohols and hydrazine hydrate catalyzed by synthesized arene Ru(II) complexes of aroylthiourea ligand. Notably, the catalytic efficiencies of six- and four-membered N,S-chelate ruthenium c

Dihydrazone compound high in affinity with Abeta protein and Tau protein, derivative thereof, and applications of dihydrazone compound and derivative

The invention provides a dihydrazone compound high in affinity with Abeta protein and Tau protein, a derivative thereof, and applications of the dihydrazone compound and the derivative. The structureof the dihydrazone compound is represented by formula I. The dihydrazone compound can be directly taken as a fluorescence probe used for detecting neurofibrillary tangles in vivo or in tissue samples;when the dihydrazone compound is adopted in nuclear medicine imaging, appropriate radioisotopes are needed for labeling. The dihydrazone compound is especially suitable to be used for diagnosis of neurodegenerative diseases, and diagnosis of patients with diseases with Abeta plaques including Alzheimer's disease.

Unusual synthesis of azines and their oxidative degradation to carboxylic acid using iodobenzene diacetate

Reaction of 3-hydrazonobutan-2-one oxime with aromatic aldehydes resulted in the formation of 1,2-bis(arylidene)hydrazine commonly referred as azine as an unexpected product, instead of expected product 3-(aryl)methylenehydrazonobutan-2-one oxime, which were subsequently oxidized to corresponding aromatic acids with an ecofriendly oxidizing agent iodobenzene diacetate. Azines and carboxylic acids were characterized by IR and NMR (1H, 13C, HMBC, and HMQC) studies.

Ligand Redox-Controlled Tandem Synthesis of Azines from Aromatic Alcohols and Hydrazine in Air: One-Pot Synthesis of Phthalazine

A controlled tandem synthetic route to azines from various alcohols and hydrazine hydrate by the use of a Ni(II) complex of 2,6-bis(phenylazo)pyridine as a catalyst is reported. In marked contrast to the previous report, the reaction is operative using an earth-abundant metal catalyst, milder reaction conditions, and aerobic conditions, which though are desirable but unprecedented in the literature. The catalytic reaction has a vast substrate scope including a single-step synthesis of phthalazine from 1,2-benzenedimethanol and hydrazine hydrate via intramolecular coupling. Mechanistic investigation suggests that the coordinated ligand redox controls the reaction by the use of a reversible azo (N=N)/ hydrazo (NH - NH) redox couple where the metal center is used primarily as a template.

C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay

In the current protocol, amine functionalized montmorillonite K10 nanoclay (NH2-MMT) was applied to catalyze the formation of C[sbnd]N bonds in the synthesis of azines and 2-aminothiazoles at room temperature. In comparison with the current methods of C[sbnd]N bond formation, this approach displays specific advantages include atom economy, clean conversion, design for energy efficiency, the use of nontoxic and heterogeneous catalyst, higher purity and yields, safer solvent and reagents for this organic transformation.

Mononuclear half-sandwich iridium and rhodium complexes through C?H activation: Synthesis, characterization and catalytic activity

A series of mononuclear half-sandwich cyclometalated group 9 (Ir and Rh) metal complexes were synthesized in good yields through metal-mediated C?H bond activation. These air-stable C, N-chelate mode complexes have similar solid state structures. Both experimental results and DFT calculations confirmed that no binuclear complexes were generated in this reaction. The iridium complex 3a exhibited good catalytic activity for the reduction of both electron-rich and electron-poor aryl imines with low catalyst loading in the presence of formic acid/triethylamine (F/T) azeotropic mixture. All complexes were fully characterized by elemental analysis and IR and NMR spectroscopies. The structures of 1a, 1b, 2a, 3a and 4b (see chemical structure formula in Scheme 1 and Scheme 2) were further confirmed by single-crystal X-ray analysis.

A Copper-Benzotriazole-Based Coordination Polymer Catalyzes the Efficient One-Pot Synthesis of (N′-Substituted)-hydrazo-4-aryl-1,4-dihydropyridines from Azines

A series of new (N′-substituted)-hydrazo-4-aryl-1,4-dihydropyridines was successfully synthesized via a facile one-pot catalytic pathway utilizing azines and propiolate esters as starting materials and a one-dimensional copper benzotriazole-based coordination polymer as catalyst. In the absence of catalyst, the corresponding 5-substituted 4,5-dihydropyrazoles were formed in moderate to high yields. Fine-tuning of the catalysts allowed us to gain more insights regarding the plausible reaction mechanism. (Figure presented.).

Selective Reduction of Azines to Benzyl Hydrazones with Sodium Borohydride Catalyzed by Mesoporous Silica-Supported Silver Nanoparticles: A Catalytic Route towards Pyrazole Synthesis

The catalytic activity of supported silver nanoparticles on mesoporous silica was studied, for the selective reduction of azines into benzyl hydrazones using sodium borohydride as mild reducing agent. Different sizes of silver nanoparticles supported on mesoporous silica (Ag/HMS) were successfully prepared by two methods, i.e., wet impregnation followed by reduction with hydrogen at 350 °C and in situ deposition/reduction with a mixture of amines (ethanolamine and ethylenediamine). The Ag/HMS (amines) catalyst was found to promote the selective 1,2-reduction of aryl-substituted azines, compared to the corresponding 1,4-reduction that occurs in general reduction processes. This catalytic transfer hydrogenation process found to be clean, fast and quantitative (>99% yields and selectivity) towards benzyl hydrazone synthesis under mild conditions. Of great importance is that under the present catalytic conditions reducible functional groups remain intact. Formal kinetics, support the in situ formation of silver hydride species being responsible for the reduction process. The presence of protic polar methanol enhanced the catalytic activity of Ag/HMS. Based on the recycling studies the catalytic system Ag/HMS-NaBH4 was found to catalyze the selective reduction of azines nine times without significant loss of its activity. Finally, a one-pot reaction between the in situ produced benzyl hydrazones and a series of nitrostyrenes readily provided the regioselective synthesis of 1,3,5-subtituted pyrazoles, highlighting a useful synthetic application of the catalytic protocol. (Figure presented.).