5328-80-3

Usage

Uses

Used in Agricultural Industry:
1-(2-chlorophenyl)-N-[(2-chlorophenyl)methylideneamino]methanimine is used as a fungicide for protecting crops from fungal infections. Its application helps in maintaining crop health and productivity by controlling a wide range of fungal pathogens.
Used in Wood and Timber Preservation:
In the wood and timber industry, 1-(2-chlorophenyl)-N-[(2-chlorophenyl)methylideneamino]methanimine is used as a preservative to protect wood from fungal decay and infestation. This helps in extending the lifespan of wooden structures and products, ensuring their durability and resistance to fungal attacks.
It is important to handle and apply this chemical with caution to avoid any potential harm, as safety precautions are essential when dealing with any chemical compounds.

InChI:InChI=1/C14H10Cl2N2/c15-13-7-3-1-5-11(13)9-17-18-10-12-6-2-4-8-14(12)16/h1-10H

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 354-58-5 1,1,1-Trichloro-2,2,2-trifluoroethane 
• 52372-78-8 2-chlorobenzaldehyde hydrazone 
• 558-13-4 carbon tetrabromide 
• 76-13-1 1,1,2-Trichloro-1,2,2-trifluoroethane 
• 82988-74-7 (2-chlorophenyl)diazomethane 
• 124-73-2 1,2-dibromo-1,1,2,2-tetrafluoroethane 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 25144-38-1 (E)-2,2'-dichlorostilbene 
• 792-39-2 bis(α,2-dichlorobenzylidene)hydrazine 
• 52372-78-8 2-chlorobenzaldehyde hydrazone 
• 74115-29-0 2-chloro-N'-(2-chloro-benzylidene)-benzohydrazonoyl chloride 
• 36951-39-0 2-chloro-benzaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 36951-46-9 2-chloro-benzaldehyde [5-(2-chloro-benzylidene)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 89-98-5 2-chloro-benzaldehyde 
• 108593-02-8 (2-Chlorphenyl)bis(methylthio)methan 
• 7647-01-0 hydrogenchloride 
• 873-32-5 2-Chlorobenzonitrile 
• 92253-52-6 N,N-Bis-(2-chlor-benzyl)-hydrazin 
• 118-91-2 ortho-chlorobenzoic acid 
• 1166381-90-3 7,14-bis(2-chlorophenyl)-11,11-dimethyl-1,4,10,12-tetraoxadispiro[4.2.5.2]pentadecane-9,13-dione 
• 1613287-95-8 C₅₀H₄₄Cl₄N₄O₄P₂ 

Relevant academic research and scientific papers

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.

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.

An efficient synthesis of perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones catalyzed by TiO2-functionalized nano-Fe3O4 encapsulated-silica particles as a reusable magnetic nanocatalyst

Immobilization of a nano-TiO2 catalyst on the surface of a magnetic SiO2 support was performed through the reaction of a Fe3O4@SiO2 composite with Ti(OC4H9)4via a simple process. The Fe3O4@SiO2-TiO2 nanocomposite was characterized using scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), Fourier transform infrared spectra (FTIR), and a vibrating sample magnetometer (VSM). The Fe3O4@SiO2-TiO2 nanocomposite has been found to be an efficient catalyst for the synthesis of perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones from the condensation of various aldazines and potassium thiocyanate in acetonitrile solvent at room temperature. It has been found that the nanocatalyst was recycled for up to 6 cycles with minimal loss in catalytic activity. The purpose of this research was to provide an easy method for the synthesis of perhydrotriazolotriazole derivatives by a robust and magnetically recoverable catalyst.

Solvent-Free Green Synthesis of Azines and Their Conversion to 2,5-Disubstituted-1,3,4-thiadiazoles

A solvent-free, clean, and efficient method has been developed for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via azines. This approach exploits the synthetic potential of clean reactions and offers many advantages such as excellent product yie

An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound

Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating.

Monohydrocyanation of symmetrical azines using potassium hexacyanoferrate(II) as an environmentally friendly cyanide source

The monohydrocyanation of symmetrical azines to synthesize α-hydrazinonitriles using potassium hexacyanoferrate(II) as cyanide source and benzoyl chloride as a promoter under catalyst-free conditions is described. The advantages of this protocol are the environmentally friendly cyanide source, high yield, and simple work-up procedure. Georg Thieme Verlag Stuttgart New York.

Synthesis and characterization of novel organonickel and organocobalt complexes via carbonechlorine bond activation

The ortho-metalated nickel(II) complexes 3, 4, 7 and 8 were obtained by the reaction of ortho-halogeno aromatic bis-Schiff bases 1, 2, 5 and 6 with the stoichiometric amount of Ni(PM-3)4. The combination of 5 and 6 with two equivalents of Ni(PM-3)4 resulted in oxidative addition of the double CeCl bonds to afford ortho-bis-chelated nickel(II) complexes 9 and 10. The reaction of 6 with Co(PM-3)4 gave rise to dinuclear ortho-metalated cobalt(II) complex 12 through CeCl bond activation while the reaction of 5 with Co(PM-3)4 delivered bis-chelated cobalt(I) complex 11 through both CeCl and CeH bond activation. The structures of complexes 3, 4, 8, 9, 11 and 12 were determined by X-ray single crystal diffraction. The catalytic activity of bis-chelated cobalt(I) complex 11 as catalyst for C,C-coupling reaction was explored.

Microwave-assisted synthesis of 1-hydrazinophosphonates via the reaction of aldazines with dialkyl phosphite

A simple, efficient, and novel method has been developed for the synthesis of 1-hydrazinophosphonic acids from aldazines. As described below, treatment of aldazines with diethyl phosphite gives the corresponding 1-hydrazinophosphonic acids in good yields. The reaction proceeds under microwave irradiation at 110°C and neutral condition without any additives such as base, acid, or catalyst. This method is easy, rapid, and gives good yields for the 1-hydrazinophosphonic acids.

Synthesis of 1H-indazole: A combination of experimental and theoretical studies

A new practical synthesis of 1H-indazole is presented. A previous mechanism for the cyclization step is proved to be nonfeasible and a hydrogen bond propelled mechanism is proposed. The new mechanism is suitable for similar cyclization, and a new reaction is predicted. Springer Science+Business Media B.V. 2012.

Spectroscopic and theoretical studies on symmetric aryl azines

Azines, which closely resemble azobenzenes, have important applications in the field of nonlinear optics. NMR and IR spectroscopic study of some symmetric aryl azines has been undertaken with the aid of ab initio theoretical calculations. All data indicated that the structure of azine and substituted azines is the symmetric trans form.