14850-96-5

Basic information

• Product Name: acetophenone benzoyl hydrazone
• CAS NO: 14850-96-5
• Molecular Weight: 238.289
• Mol File: 14850-96-5.mol

Chemical Properties

• CAS DataBase Reference: acetophenone benzoyl hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: acetophenone benzoyl hydrazone(14850-96-5)
• EPA Substance Registry System: acetophenone benzoyl hydrazone(14850-96-5)

Safety Data

• Hazardous Substances Data: 14850-96-5(Hazardous Substances Data)

Upstream product

• 7654-03-7 N′-(1-phenylethyl)benzohydrazide 
• 98-86-2 acetophenone 
• 613-94-5 benzoic acid hydrazide 
• 536-74-3 phenylacetylene 
• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 
• 126382-70-5 benzoylacetaldehyde benzoylhydrazone 
• 41804-90-4 N-Benzoyl-N-trifylhydrazin 
• 585-71-7 (1-bromoethyl)benzne 

Downstream Products

• 85452-67-1 1-benzoyl-3-phenyl-5-(4-tolyl)pyrazole 
• 25445-77-6 4-phenyl-1,2,3-thiadiazole 
• 98-88-4 benzoyl chloride 
• 98-86-2 acetophenone 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 142068-35-7 (R)-(+)-1-phenyl-1-(2-benzoylhydrazino)ethane 
• 142068-32-4 (S)-(-)-1-phenyl-1-(2-benzoylhydrazino)ethane 
• 256479-24-0 CH₃C(C₆H₅)NNHC(O)C₆H₅Cu(H₂O)2(SO₄)*H₂O 
• 1158075-09-2 trans-[Ru(III)(C₆H₄C(Me)NNC(O)Ph)(PPh₃)2Cl] 
• 385819-29-4 bis(acetophenone benzoylhydrazone)cadmium(II) chloride monohydrate 
• 385819-25-0 bis(acetophenone benzoylhydrazone)copper(II) chloride monohydrate 
• 385819-20-5 bis(acetophenone benzoylhydrazone)cobalt(II) chloride monohydrate 
• 385819-22-7 bis(acetophenone benzoylhydrazone)nickel(II) chloride monohydrate 

Relevant articles and documents

TEMPO-mediated Aza-diels-alder reaction: Synthesis of tetrahydropyridazines using ketohydrazones and olefins

A novel, facile, and efficient method for the synthesis of tetrahydropyridazines by a one-pot tandem reaction of easily accessible ketohydrazones and olefins in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) has been successfully developed. The reaction involves the initial generation of azoalkenes from direct oxidative dehydrogenation of ketohydrazones using TEMPO as the commercially available oxidant, followed by a subsequent aza-Diels-Alder reaction with olefins.

Synthesis, crystallographic, computational and molecular docking studies of new acetophenone-benzoylhydrazones

Three aroylhydrazones, acetophenone-Benzoylhydrazone (I), p-hydroxy-acetophenone-benzoylhydrazone (II) and p-nitro- acetophenone-benzoylhydrazone (III) have been synthesized and further analyzed with the aid of IR, UV-Vis, and NMR spectroscopic and X-ray Crystallographic techniques. The optimized molecular structures were determined by Density Functional Theory (DFT) using the B3LYP function comprising the 6-311++G (2d, 2p) basis set. The calculated and experimental results for the NMR spectroscopic technique were observed to be consistent. The two reported crystals are monoclinic in the same space group of P21/c. Hirshfeld surface analyses revealed H···H as the most important intermolecular interactions in compounds II and III. The molecular docking of the compounds against three enzymes - aldose reductase, aldehyde reductase, and β-glucosidase were also carried out where compound III displayed the best inhibition of the enzymes with a binding energy of -11.30, -9.58 and -11.10 Kcal mol?1 against aldose reductase, aldehyde reductase, and β- glucosidase respectively.

Efficient [(NHC)Au(NTf2)]-catalyzed hydrohydrazidation of terminal and internal alkynes

The efficient hydrohydrazidation of terminal (6a–r, 18 examples, 0.1–0.2 mol % [(NHC)Au(NTf2)], T = 60 °C) and internal alkynes (7a–j, 10 examples, 0.2–0.5 mol % [(NHC)Au(NTf2)], T = 60–80 °C) utilizing a complex with a sterically demanding bispentiptycenyl-substituted NHC ligand and the benign reaction solvent anisole, is reported.

I2-Promoted [4 + 2] cycloaddition of: In situ generated azoalkenes with enaminones: Facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines

A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judici

Copper catalyzed cyanomethylation reaction of 4-thiazolidinone

An effective copper catalyzed Cross Dehydrogenative Coupling (CDC) reaction of 4-thiazolidinones with acetonitrile has been developed. The described strategy undergoes radical pathway by employing copper, oxidant and easily available acetonitrile as a cya

Copper catalysed cross-dehydrogenative coupling (CDC) reaction of 4-thiazolidinone with terminal alkyne

Cross dehydrogenative coupling (CDC) strategy has been employed for C-alkynylation of 4-thiazolidinone with terminal alkyne under copper catalysis. Present reaction involves coupling of C(sp3) adjacent to sulfur of 4-thiazolidinone with C(sp) of terminal alkyne under CDC strategy is unprecedented to the best of our knowledge. Significant functional group tolerance, considerable yield and DFT study for mechanism make this synthetic task more interesting and compatible.

Acetophenone benzoylhydrazones as antioxidant agents: Synthesis, in vitro evaluation and structure-activity relationship studies

Acetophenone and its analogues are naturally-occurring compounds found in many foods and plants. In this study, a series of acetophenone benzoylhydrazones 5a-o were designed and synthesized as new potential antioxidant agents. Designed molecules contain hydrazone and phenolic hydroxyl moieties which possibly contribute to antioxidant activity. The antioxidant properties of compounds 5a-o in terms of reducing ability and radical-scavenging activity were assessed by using FRAP and DPPH tests, respectively. While the unsubstituted compound 5a had the superior capacity in the FRAP assay, the 2,4-dihydroxyacetophenone analogue 5g was the most potent radical scavenger in the DPPH method. The antioxidant potential of representative compounds 5a and 5g was further confirmed by TEAC and ORAC assays. Cell viability assays revealed that while the promising compounds 5a and 5g had no significant toxicity against HepG2 and NIH3T3 cells, they potently protected HepG2 cells against H2O2-induced oxidative damage at low concentrations. Furthermore, spectroscopic studies with different biometals demonstrated that 5g was able to interact with Cu2+ to form a 1:1 complex.

Palladium-Catalyzed Carbonylative Synthesis of 3-Methyleneisoindolin-1-ones from Ketimines with Hexacarbonylmolybdenum(0) as the Carbon Monoxide Source

An interesting procedure for the palladium-catalyzed carbonylative synthesis of 3-methyleneisoindolin-1-ones from ketimines was established. By using Mo(CO)6 (0.3 equiv.) as the solid CO source and through C(sp2)?H bond activation, t

Transfer hydrogenation of ketones catalysed by half-sandwich (η6-p-cymene) ruthenium(II) complexes incorporating benzoylhydrazone ligands

Neutral half-sandwich η6-p-cymene ruthenium(II) complexes of general formula [Ru(η6-p-cymene)Cl(L)] (HL?=?monobasic O, N bidendate benzoylhydrazone ligand) have been synthesized from the reaction of [Ru(η6-p-cymene)(μ-Cl)Cl]2 with acetophenone benzoylhydrazone ligands. All the complexes have been characterized using analytical and spectroscopic (Fourier transform infrared, UV–visible, 1H NMR, 13C NMR) techniques. The molecular structures of three of the complexes have been determined using single-crystal X-ray diffraction, indicating a pseudo-octahedral geometry around the ruthenium(II) ion. All the ruthenium(II) arene complexes were explored as catalysts for transfer hydrogenation of a wide range of aromatic, cyclic and aliphatic ketones with 2-propanol using 0.1?mol% catalyst loading, and conversions of up to 100% were obtained. Further, the influence of other variables on the transfer hydrogenation reaction, such as base, temperature, catalyst loading and substrate scope, was also investigated.

Synthesis and characterisation of cycloruthenated benzhydrazone complexes: Catalytic application to selective oxidative cleavage of olefins to aldehydes

A simple and convenient method to synthesise new air-stable cyclometalated ruthenium(ii) complexes from the reaction of p-substituted acetophenone benzhydrazide ligands and [RuHCl(CO)(AsPh3)3] has been described. The complexes have been characterised by various methods, including elemental analysis, FT-IR, NMR (1H and 13C) and UV-vis. The molecular structures of complexes 3 and 4 have been determined by singlecrystal X-ray diffraction analysis which indicates the tridentate coordination mode of the ligand and the presence of a distorted octahedral geometry around the ruthenium ion. The complexes have been found to be a highly active catalytic system in the selective oxidative cleavage of a wide range of alkenes and alkynes in the presence of NaIO4 as an oxidant. Notably, the desired aldehyde products were obtained with high conversions and yields using 0.5 mol% catalyst loading within 30 min at room temperature. Furthermore, the influence of reaction parameters such as solvents, oxidants, temperature and catalyst loading was also investigated.