80355-74-4

Usage

Uses

Used in Coordination Chemistry:
(1E)-bis(2-methylbenzylidene)hydrazine is used as a ligand for the formation of coordination compounds. Its ability to chelate with metal ions allows for the creation of stable complexes with potential applications in various fields.
Used in Organic Synthesis:
(1E)-bis(2-methylbenzylidene)hydrazine is employed as a synthetic building block in organic chemistry. Its reactivity and structural features make it a valuable component in the synthesis of various organic compounds.
Used in Metal-Organic Frameworks (MOFs):
(1E)-bis(2-methylbenzylidene)hydrazine is utilized as a component in the construction of metal-organic frameworks. These porous materials have potential applications in gas storage, catalysis, and drug delivery due to their high surface area and tunable properties.
Used in Pharmaceutical Research:
(1E)-bis(2-methylbenzylidene)hydrazine is studied for its biological activity, particularly as an anti-cancer agent. Its potential to target and inhibit the growth of cancer cells is under investigation, although further research is needed to fully understand its therapeutic potential and associated risks.

Upstream product

• 698-20-4 1-(diazomethyl)-2-methylbenzene 
• 529-19-1 2-Methylbenzonitrile 
• 52023-52-6 N,N,N',N'-tetraformylhydrazine 
• 108-88-3 toluene 
• 354-48-3 1,1,1-tribromotrifluoroethane 
• 529-20-4 2-methylphenyl aldehyde 
• 35629-84-6 N'-(2-methylbenzylidene)-4-methylbenzenesulfonohydrazide 

Downstream Products

• 134898-22-9 o-tolualdehyde azine-5,5'-disulfonyl chloride 
• 1613287-97-0 C₅₄H₅₆N₄O₄P₂ 
• 134898-14-9 N,N'-Bis-[1-[5-(3,5-dimethyl-morpholine-4-sulfonyl)-2-methyl-phenyl]-meth-(E)-ylidene]-hydrazine 
• 134898-13-8 2-methyl-5-N,N-dimethylsulfamoylbenzaldehyde azine 
• 529-20-4 2-methylphenyl aldehyde 

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.

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.

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 N-imino-β-lactams from 2,3-diaza-1,3-dienes (azines) mediated by POCl3

Symmetrically substituted azines derived from aromatic aldehydes have been found compatible with the reaction of phenoxyacetic acid activated by POCl 3. N-Imino-β-lactams are efficiently obtained by this method in good to excellent yields with varying levels of cis, trans-selectivity.

The catalytic olefination reaction of aldehydes and ketones with CBr 3CF3

The new approach of catalytic olefination reaction (COR) has been used to convert aromatic and aliphatic aldehydes and ketones to 2-bromo-3,3,3- trifluoroprop-1-enes by the treatment of corresponding hydrazones with CBr 3CF3 under copper(I) catalysis conditions. The reaction proceeds stereoselectively, the target alkenes were obtained in good yields.

Orthoamide, LX [1]. N,N,N',N'-Tetraformylhydrazine- a Formylation Agent for Aromatic Compounds of Wide Scope

The reagent system formed from N,N,N',N'-tetraformylhydrazine (3) and aluminum chloride allows the formylation of aromatic compounds. The scope of the method is comparable with the Olah formylation and the Gross-Rieche procedure, since benzene and fluorobenzene can be formylated. Two formyl groups are transferred from 3 to the aromatic nuclei when a molar ratio 4:1:4 (aluminum chloride/3/aromatic compound) is chosen.

Oxidative Transformations of Aldazines and Ketazines with Organic Peroxyacids

Oxidation of aromatic aldazines and ketazines with various peroxycarboxylic acids was investigated.It was found that one part of azine molecule 2 was converted into carbonyl compound 1 or related acid 3 while the second part was transformed into carboxylic ester 4 related to peroxyacid used as an oxidant.It was revealed that aromatic azines could be used as a source of diazaarylmethanes and mechanisms of reactions studied were postulated. aldazines, carboxylic esters, ketazines, oxidation, peroxycarboxylic acids

CHLOROSULFONATION OF DIARYL AZINES

Benzaldehyde- and o-, m-, p-anisaldehyde azines; thiophene-2-carboxaldehyde, and biphenyl-4-carboxaldehyde azines (1-8) reacted with excess chlorosulfonic acid to give the disulphonyl chlorides (1a-8a).These were condensed with amines and hydrazine to give 27 derivatives, (Table I) for biocidal evaluation.The orientation of sulfonation is discussed in relation to the stereoelectronic factors and the spectral data.Attempted chlorosulfonation of furan-2-carboxaldehyde azine (9) gave an impure product which could not be clearly characterized as the morpholidate derivative.

ZEOLITE-CuNaY CATALYZED DECOMPOSITION OF ARYLDIAZOMETHANE

Decomposition of aryldiazomethanes is catalyzed by copper ion-exchanged Y-type zeolite to afford cis-1,2-diarylethylenes in high selectivity.The catalytic activity and selectivity are found to be affected by the exchange level of copper ions in zeolite and the solvent used.