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Usage

Uses

Used in Organic Synthesis:
Benzil dihydrazone is used as a reagent for the preparation of hydrazones, which are important intermediates in the synthesis of various organic compounds. Its ability to form stable complexes with metal ions also makes it a valuable component in the development of new synthetic pathways.
Used in Analytical Chemistry:
As a ligand, benzil dihydrazone is employed in coordination chemistry for the determination of aldehydes and ketones. Its complex-forming properties with metal ions contribute to its use in analytical techniques, enhancing the detection and quantification of specific compounds.
Used in Corrosion Inhibition:
In industrial applications, benzil dihydrazone serves as a corrosion inhibitor, protecting materials from degradation and extending their service life. Its effectiveness in this role is attributed to its ability to form protective layers and reduce the rate of chemical reactions that lead to corrosion.
Used in Metal Extraction:
Benzil dihydrazone is utilized as a chelating agent in metal extraction processes. Its affinity for metal ions allows for selective binding and separation of metals from complex mixtures, streamlining the extraction and purification of valuable elements.
Overall, benzil dihydrazone's multifaceted applications across different industries underscore its importance as a versatile chemical compound with significant potential for further development and innovation.

InChI:InChI=1/C14H14N4/c15-17-13(11-7-3-1-4-8-11)14(18-16)12-9-5-2-6-10-12/h1-10H,15-16H2/b17-13-,18-14+

Upstream product

• 64-17-5 ethanol 
• 110411-27-3 benzil-mono-benzylidenehydrazone 
• 7803-57-8 hydrazine hydrate 
• 134-81-6 benzil 
• 632-51-9 1,1,2,2-tetraphenylethylene 
• 7381-16-0 1,2-disodiotetraphenylethane 
• 1489-06-1 2,3-diphenyl-5,6-dihydropyrazine 
• 3893-33-2 benzil monoazine 

Downstream Products

• 30506-03-7 1,2-bis(1,2-diphenylethylidene)hydrazine 
• 91666-82-9 2,3,6,7-tetraphenyl<1,2,3>triazolo<2,1-a><1,2,3>triazole 
• 501-65-5 diphenyl acetylene 
• 134-81-6 benzil 
• 302-01-2 hydrazine 
• 451-40-1 phenyl benzyl ketone 
• 484-47-9 lophine 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 1608-10-2 1,2,3,4-tetraphenyl-1,3-butadiene 
• 55255-22-6 9,14-dihydro-9-phenyldibenz[a,c]anthracene 
• 13892-81-4 (Z)-1-(acetoxy)-1,2-diphenylethylene 
• 7664-41-7 ammonia 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 103571-18-2 3,4-bis-benzo[1,3]dioxol-5-yl-7,8-diphenyl-[1,2,5,6]tetrazocine 

Relevant academic research and scientific papers

Novel benzildihydrazone based Schiff bases: Syntheses, characterization, thermal properties, theoretical DFT calculations and biological activity studies

A novel series of benzildihydrazone derived Schiff base compounds having electron-accepting and donor-donating appendices were synthesized. A combined experimental and theoretical analysis was conducted to elucidate all the characteristic and structural features of the synthesized molecules. The experimental characterizations were performed by using FT-IR, 1H/13C NMR, mass spectroscopic techniques, and X-ray diffraction methods. The thermal stabilities of the molecules were evaluated by thermal gravimetric analysis (TGA) and all them were found to be stable above 300 °C. To support the experimental, structural, and spectroscopic data of the dyes, the quantum chemical parameters were obtained within the density functional theory (DFT) calculations. In addition, some properties based on the HOMO and LUMO energies and the temperature dependence of some thermodynamic quantities (i.e. entropy, heat capacity, and enthalpy) were also studied. According to the antimicrobial activity evaluation results, compound 1f has been found to be potentially effective in suppressing microbial growth of bacteria with variable potency. The DNA cleavage activity of the compounds was analysed by gel electrophoresis assay. The results showed that the compounds have DNA cleaving activity.

Synthesis and characterization of Schiff base octaazamacrocyclic complexes and their biological studies

A condensation reaction between 1,2-diphenylethane-1,2-dione dihydrazone (DPEDDH) and dimethyl or diethyloxalate in methanol resulted in a novel Schiff base octaazamacrocyclic ligand, (L): (6,7,14,15-tetraoxa-2,3,10,11-tetraphenyl-1,4,5,8,9,12,13,16-octaazacyclohexadecane-1,3,9,11-tetraene). Subsequently metal complexes of the type [MLX2] and [CuL]X2; (M = Mn(II), Co(II), Ni(II) and Zn(II); X = Cl or NO3) were synthesized by the reaction of the free macrocyclic ligand (L) with the corresponding metal salts in 1:1 molar ratio. These complexes were characterized on the basis of analytical data, molar conductivity and magnetic susceptibility measurements, ESI-mass, IR, NMR (1H and 13C), EPR and electronic spectral studies. The thermal stability of the complexes was also studied by TGA and DTA analyses. These studies show that all the complexes have octahedral arrangement around the metal ions except copper complexes which are square planar. The ligand and its complexes were screened for their antibacterial activity in vitro against Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria and were also studied for their anticancer activity against the human cancer cells lines: HeLa (Human cervical carcinoma), MCF7 (Human breast adenocarcinoma) and Hep3B (Human Hepatocellular carcinoma). The recorded IC50 values for the tested compounds show moderate to good cytotoxicity against these cancer cell lines. The copper complex, [CuL]Cl2, showed excellent antimicrobial activity against tested microorganisms which is almost equivalent to the standard drug ciprofloxacin.

Synthesis of new macrocyclic complexes of transition metals: Structural characterization and biological activity

Condensation reaction between benzildihydrazone and pyridine 2,3-dicarboxylic acid, pyridine 3,4-dicarboxylic acid or pyridine 2,4-dicarboxylic acid in methanol led to novel Schiff base macrocyclic ligands L1, L2, and L3 respectively. Metal complexes of the type [MLCl2], [M = Co(II), Ni(II)], were synthesized by the reaction of a free macrocyclic ligand (L) with the corresponding metal salts in a 1 : 1 molar ratio. The complexes were characterized on the basis of analytical data, molar conductivity and magnetic susceptibility measurements, IR, 1H, and 13C NMR, and electronic spectral data. Those demonstrated that all the complexes had octahedral arrangement around the metal ions. The ligand and its complexes were screened for their antibacterial, antifungal and DNA cleavage activities. The studies demonstrate that the complexes possessed antimicrobial and DNA cleavage activities.

Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

Eight novel Schiff bases derived from benzil dihydrazone (BDH) or benzil monohydrazone (BMH) and four fused-ring carbonyl compounds (3-formylindole, FI; 3-acetylindole, AI; 3-formyl-1-methylindole, MFI; 1-formylnaphthalene, FN) were synthesized and characterized by elemental analysis, ESI-QTOF-MS, 1H and 13C NMR spectroscopy, as well as single-crystal X-ray diffraction. They are (1Z,2Z)-1,2-bis{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFI), C32H24N6, (1Z,2Z)-1,2-bis{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethane (BDHAI), C34H28N6, (1Z,2Z)-1,2-bis{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BMHMFI) acetonitrile hemisolvate, C34H28N6·0.5CH3CN, (1Z,2Z)-1,2-bis{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFN), C36H26N4, (Z)-2-{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFI), C23H17N3O, (Z)-2-{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethanone (BMHAI), C24H19N3O, (Z)-2-{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHMFI), C24H19N3O, and (Z)-2-{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFN) C25H18N2O. Moreover, the in vitro cytotoxicity of the eight title compounds was evaluated against two tumour cell lines (A549 human lung cancer and 4T1 mouse breast cancer) and two normal cell lines (MRC-5 normal lung cells and NIH 3T3 fibroblasts) by MTT assay. The results indicate that four (BDHMFI, BDHFN, BMHMFI and BMHFN) are inactive and the other four (BDHFI, BDHAI, BMHFI and BMHAI) show severe toxicities against human A549 and mouse 4T1 cells, similar to the standard cisplatin. All the compounds exhibited weaker cytotoxicity against normal cells than cancer cells. The Swiss Target Prediction web server was applied for the prediction of protein targets. After analyzing the differences in frequency hits between these active and inactive Schiff bases, 18 probable targets were selected for reverse docking with the Surflex-dock function in SYBYL-X 2.0 software. Three target proteins, i.e. human ether-á-go-go-related (hERG) potassium channel, the inhibitor of apoptosis protein 3 and serine/threonine-protein kinase PIM1, were chosen as the targets. Finally, the ligand-based structure-activity relationships were analyzed based on the putative protein target (hERG) docking results, which will be used to design and synthesize novel hERG ion channel inhibitors.

Graphene oxide (GO) or reduced graphene oxide (rGO): Efficient catalysts for one-pot metal-free synthesis of quinoxalines from 2-nitroaniline

A straightforward one-pot preparation of library of quinoxalines from 2-nitroanilines under entirely metal-free conditions is described. Initial reduction of nitroaniline with hydrazine hydrate is efficiently catalyzed by graphene oxide (GO) or reduced graphene oxide (rGO), and further one-pot tandem reactions with 1,2-dicarbonyl compounds or with α-hydroxy ketones afford quinoxalines in excellent yields. The catalyst is recovered, characterized, and found to be recyclable for consecutive four runs examined with appreciable conversions.

Synthesis, spectral characterization and in vitro microbiological evaluation of novel glyoxal, biacetyl and benzil bis-hydrazone macrocyclic Schiff bases and their Co(II), Ni(II) and Cu(II) complexes

A series of binuclear Co(II), Ni(II) and Cu(II) complexes were synthesized by the template condensation of glyoxal, biacetyl or benzil bis-hydrazide, 2,6-diformyl-4-methylphenol and Co(II), Ni(II) or Cu(II) chloride in a 2:2:2 M ratio in ethanol. These 22-membered macrocyclic complexes were characterized by elemental analyses, magnetic, molar conductance, spectral, thermal and fluorescence studies. Elemental analyses suggest the complexes have a 2:1 stoichiometry of the type [M2LX2]·nH2O and [Ni2LX22H2O]·nH2O (where M = Co(II) and Cu(II); L = H2L1, H2L 2 and H2L3; X = Cl; n = 2). From the spectroscopic and magnetic studies, it has been concluded that the Co(II) and Cu(II) complexes display a five coordinated square pyramidal geometry and the Ni(II) complexes have a six coordinated octahedral geometry. The Schiff bases and their metal complexes have also been screened for their antibacterial and antifungal activities by the MIC method.

STUDIES ON THE OXIDATION OF HYDRAZONES WITH IODINE AND WITH PHENYLSELENENYL BROMIDE IN THE PRESENCE OF STRONG ORGANIC BASES; AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF VINYL IODIDES AND PHENYL-VINYL SELENIDES

The oxidation of hydrazones by iodine in the presence of strong organic bases (guanidines) has been studied.Improved yields of vinyl iodides can be obtained by inverse addition using dry solvents and with a final heating period where appropriate.The reaction has been extended to various dihydrazones with interesting results.In complementary studies hydrazones have been oxidized by phenylselenyl bromide in the presence of strong organic bases to give the corresponding phenyl vinyl selenides in good yield.

Stereochemistry of the Acetoxymercuration of Alkynes. A Synthesis of Vinyl Acetates

The stereochemistry of acetoxymercuration of 3-hexyne has been established as antarafacial on the basis of an X-ray crystallographic study.Acetoxymercuration of diphenylacetylene afforded (Z)-α-acetoxy-β-(acetoxymercuri)stilbene by a suprafacial addition of Hg(OAc)2.A simple method for the in situ acetoxymercuration-demercuration of dialkyl-substituted alkynes to afford vinyl acetates is described.The sodium borohydride reduction of vinyl mercurials was shown to produce divinyl mercurials while demercuration with zinc dust in acetic acid provided a useful method for the preparation of vinyl acetates.