588-64-7

Usage

Uses

Used in Scientific Research:
Benzaldehyde Phenylhydrazone is used as a reagent in the field of organic synthesis for the creation of more complex molecules. Its role as a building block is crucial in developing new organic compounds with potential applications in various industries.
Used in Organic Synthesis:
In the realm of organic synthesis, Benzaldehyde Phenylhydrazone is employed as a key intermediate, facilitating the synthesis of a wide range of organic compounds. Its unique structure and reactivity make it a valuable component in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Optical and Electronic Applications:
Leveraging its photoluminescent properties, Benzaldehyde Phenylhydrazone is utilized in the development of materials for optical and electronic applications. This includes its potential use in the creation of light-emitting diodes (LEDs), sensors, and other optoelectronic devices that require materials with specific light-emitting characteristics.
Used in Material Science:
BENZALDEHYDE PHENYLHYDRAZONE's photoluminescent properties also make it a candidate for material science research, where it can be explored for use in the development of new materials with unique optical and electronic properties, contributing to advances in technology and industry.

InChI:InChI=1/C13H12N2/c1-3-7-12(8-4-1)11-14-15-13-9-5-2-6-10-13/h1-11,15H/b14-11+

Upstream product

• 186581-53-3 diazomethane 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 17384-37-1 acetic acid-(benzylidene-phenyl-hydrazide) 
• 925-90-6 ethylmagnesium bromide 
• 64-17-5 ethanol 
• 861336-72-3 1-phenyl-1-m-toluidino-pentan-3-one 
• 59-88-1 phenylhydrazine hydrochloride 
• 39143-05-0 (Z)-4-benzylidene-3-methyl-1-phenyl-1H-pyrazolidinyl-5(4H)-ketone 
• 100-63-0 phenylhydrazine 
• 1088-32-0 3-phenyl-4-(1-phenylmethylidene)-5-isoxazolone 
• 3376-26-9 N-Benzylidenebenzylamine N-oxide 
• 857798-10-8 3,3'-benzylidene-bis-imidazo[1,2-a]pyridin-2-one 
• 538-51-2 benzylidene phenylamine 

Downstream Products

• 4430-12-0 (phenylazo)benzaldoxime 
• 583-46-0 5-benzylidene-2-thiohydantoin 
• 111709-02-5 ethyl 3-benzylidene-2-phenylcarbazate 
• 17384-37-1 acetic acid-(benzylidene-phenyl-hydrazide) 
• 62256-38-6 benzaldehyde-(2,4-diphenyl semicarbazone) 
• 2273-08-7 1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-thione 
• 100-52-7 benzaldehyde 
• 5330-70-1 pyruvic acid phenylhydrazone 
• 787-84-8 N'-benzoylbenzohydrazide 
• 109504-83-8 cyano-acetic acid-(benzylidene-phenyl-hydrazide) 
• 22632-90-2 4-methyl-benzophenone-imine 
• 18039-45-7 2,5-diphenyl-2H-tetrazole 
• 62-53-3 aniline 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Dual-parameter correlations on rate of dehydration step of a condensation reaction in aqueous solutions of ethanol, propan-2-ol and 2-methylpropan-2-ol

The reaction kinetics of the dehydration step of the condensation reaction between phenylhydrazine and benzaldehyde was studied spectrophotometrically in aqueous solutions of ethanol, propan-2-ol and 2-methylpropan-2-ol at pH 11.5 at 25 °C. The apparent second-order rate constants k2app of the reaction increase with mole fraction of water in all the aqueous solutions. Single-parameter correlations of log k2app versus π* (dipolarity/polarizability), α (hydrogen-bond donor acidity) and ETN (normalized polarity parameter) were obtained in all the aqueous solutions. In all cases, the correlations versus ETN and π* are acceptable, but correlations versus α are poor (e.g. in aqueous solutions of ethanol the correlation coefficients are 0.964, 0.967, and 0.751 respectively). The results of dual-parameter correlations of log k2app versus π* and α in all cases represent improvements with regard to the single-parameter models (in aqueous solutions of ethanol r = 0.995; s.e. = 0.038; n = 13). The apparent second-order rate constants of the reaction increase with α, π* and ETN. Increasing the hydrogen-bond donor acidity of the solvent stabilizes the activated complex of the reaction via hydrogen-bond formation with the intermediate. A dual-parameter equation of log k2app versus π* and α was obtained for the combined data set of aqueous solutions (n = 35, r = 0.989, s.e. = 0.062, F2.32 = 719.21), in which π* has the major effect on the reaction rate relative to α. Copyright

METHODS OF FORMING IMINES, IMINE-RELATED AND IMINE-DERIVED COMPOUNDS USING GREEN SOLVENTS

The present disclosure relates to using green solvents to synthesize an array of imines, imine-related and imine-derived compounds in an efficient and eco-friendly matter, satisfying green chemistry requirements. Reaction embodiments are performed using solvents, such as ethyl lactate and dimethyl isosorbide, which are both individually characterized as green. In embodiments, solvents include lactic whey and/or water as co-solvents. In these green solvents, the synthesis process discussed herein can produce up to quantitative yields of product at room temperature in a short duration. Embodiments include a method of forming an imine, imine-related or imine-derived compound product. In embodiments, the methods include mixing an aldehyde reactant with a nucleophilic/nitrogen-containing reactant in a green solvent at a temperature between negative twenty degrees Celsius (?20° C.) and positive fifty degrees Celsius (50° C.); stirring the mixture; and forming an imine, imine-related or imine-derived compound product.

1, 3-diaryl-1, 2, 4-triazole compound as well as preparation method and application thereof

The invention discloses a 1, 3-diaryl-1, 2, 4-triazole compound, which has a novel structure shown in a structural general formula I and has better selective inhibition activity on HDAC6. The invention also discloses a preparation method of the compound, aryl groups and 4-amino-N-hydroxy-benzamide groups are introduced to a 1, 2, 4-triazole matrix for modification, a series of compounds with novelstructures are synthesized, and the method has the advantages of mild reaction conditions, simple operation, high yield and the like. The invention also discloses an application of the compound in preparation of a medicine for selectively inhibiting HDAC6. The compound provided by the invention can significantly inhibit HDAC6, the IC50 value of the compound is at a nanomole level, the dosage of apatient is favorably reduced, and the toxic and side effects of the medicine on a human body are reduced. The compound provided by the invention has high selectivity on subtype HDAC1, can effectivelyavoid toxic and side effects of a drug on normal tissues of a human body, and shows good development potential.

Identification of novel 1,3-diaryl-1,2,4-triazole-capped histone deacetylase 6 inhibitors with potential anti-gastric cancer activity

Histone deacetylase 6 (HDAC6) has emerged as a critical regulator of many cellular pathways in tumors due to its unique structure basis and abundant substrate types. Over the past few decades, the role played by HDAC6 inhibitors as anticancer agents has sparked great interest of biochemists worldwide. However, they were less reported for gastric cancer therapy. In this paper, with the help of bioisosteric replacement, in-house library screening, and lead optimization strategies, we designed, synthesized and verified a series of 1,3-diaryl-1,2,4-triazole-capped HDAC6 inhibitors with promising anti-gastric cancer activities. Amongst, compound 9r displayed the best inhibitory activity towards HDAC6 (IC50 = 30.6 nM), with 128-fold selectivity over HDAC1. Further BLI and CETSA assay proved the high affinity of 9r to HDAC6. In addition, 9r could dose-dependently upregulate the levels of acetylated α-tubulin, without significant effect on acetylated histone H3 in MGC803 cells. Besides, 9r exhibited potent antiproliferative effect on MGC803 cells, and promoted apoptosis and suppressed the metastasis without obvious toxicity, suggesting 9r would serve as a potential lead compound for the development of novel therapeutic agents of gastric cancer.

Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes

A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.

Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs

A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is

Synthesis of 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) and 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) Perchlorates

Abstract: New bis-formazans and bis(5,6-dihydro-1,2,4,5-tetrazin-1-ium) perchlorates were synthesized with high yields under mild conditions. 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) were obtained by diazo coupling of para-substituted benzaldehyde phenylhydrazones with [1,1′-biphenyl]-4,4′-bis(diazonium chloride). Treatment of the obtained bis-formazans with formaldehyde in the presence of perchloric acid in dioxane afforded 1,1′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) diper-chlorates. The structure of the synthesized compounds was confirmed by elemental analyses and UV, IR, and 1H and 13C NMR spectra.

Broad-Spectrum Antifungal Agents: Fluorinated Aryl- and Heteroaryl-Substituted Hydrazones

Fluorinated aryl- and heteroaryl-substituted monohydrazones displayed excellent broad-spectrum activity against various fungal strains, including a panel of clinically relevant Candida auris strains relative to a control antifungal agent, voriconazole (VRC). These monohydrazones displayed less hemolysis of murine red blood cells than that of VRC at the same concentrations, possessed fungicidal activity in a time-kill study, and exhibited no mammalian cell cytotoxicity. In addition, these monohydrazones prevented the formation of biofilms that otherwise block antibiotic effectiveness and did not trigger the development of resistance when exposed to C. auris AR Bank # 0390 over 15 passages.

Nitrogen-modified graphene as a metal-free carbocatalyst for the solvent-free oxidative homo- and heterocoupling of amines

In this study, graphene oxide (GO) has been prepared using Hammers’ method and the produced GO was converted to nitrogen-modified GO (NGO) using hydrothermal reaction with ammonia and hydrazine. The morphology of the product was confirmed with FESEM images and XRD, TEM, Raman, TGA, EDS, BET and FTIR analyses were employed to study the structure and properties of the product. The produced NGO has been employed as a catalyst for oxidative coupling of amines to imines. The reaction was carried out at 110?°C, using 4 wt% of catalyst (versus the used amine), oxygen gas as oxidative agent, solvent-free condition in 4?h with 80% yield. To determine the versatility of the reaction, different derivatives of amines such as benzylamine, phenyl hydrazine, aniline, ethylenediamine, ethanol amine and homoveratrylamine have been examined in this reaction and successfully converted to the related imines via heterocoupling reactions. Finally, the recyclability of the reaction was investigated and the results showed only 10% decreasing in the yield after 6 runs.

Polyaromatic hydrocarbon derivatized azo-oximes of cobalt(iii) for the ligand-redox controlled electrocatalytic oxygen reduction reaction

A pair of ligands HLPyr1a and HLAnc1b (Pyr = pyrene, Anc = anthracene) incorporating π-electron-rich polycyclic aromatic hydrocarbons (PAHs), viz. pyrene and anthracene moieties respectively, in conjunction with electron-poor azo-oxime groups was synthesized. The tris complexes [CoIII(LPyr)3] 2a and [CoIII(LAnc)3] 2b were also prepared and structurally authenticated by X-ray diffraction. They exhibit significant redox and optoelectronic properties, which were analyzed by density functional theory (DFT) and time dependent density functional theory (TD-DFT). Theoretical investigation further revealed that the coordinated ligands act as superior electron reservoirs in comparison to the free ligands and transfer electrons through the PAH moieties. This property was smartly exploited to scrutinize the aptitude of the cobalt(iii) complexes for the electrocatalytic oxygen reduction reaction (ORR). The catalytic process proceeds via a 4-electron transfer pathway to form hydroxide ions in alkaline medium. The role of the PAHs in the complexes 2a and 2b in providing a pool of electrons was further emphasized via substituting them with phenyl groups, as in [CoIII(LPh)3] 2c, when the catalytic ORR activity was significantly diminished. Moreover, the activity was completely lost when the PAHs were replaced by methyl groups, as in [CoIII(LMe)3] 2d.