16435-03-3

Basic information

• Product Name: Benzaldehyde, 4-hydroxy-, phenylhydrazone
• CAS NO: 16435-03-3
• Molecular Formula: C13H12N2O
• Molecular Weight: 212.251
• Mol File: 16435-03-3.mol

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 4-hydroxy-, phenylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 4-hydroxy-, phenylhydrazone(16435-03-3)
• EPA Substance Registry System: Benzaldehyde, 4-hydroxy-, phenylhydrazone(16435-03-3)

Safety Data

• Hazardous Substances Data: 16435-03-3(Hazardous Substances Data)

Upstream product

• 58336-40-6 p-hydroxybenzaldehyde semicarbazone 
• 64-19-7 acetic acid 
• 100-63-0 phenylhydrazine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 108-98-5 thiophenol 
• 59-88-1 phenylhydrazine hydrochloride 
• 64-17-5 ethanol 

Downstream Products

• 151358-47-3 3,3'-((4-hydroxyphenyl)methylene)bis(1H-indole) 
• 13639-20-8 monopotassium para-hydroxybenzoate 
• 97936-00-0 5-(4-Chloro-phenyl)-3-(4-hydroxy-phenyl)-1-phenyl-tetrahydro-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 97935-85-8 3-(4-Hydroxy-phenyl)-5-(4-methoxy-phenyl)-1-phenyl-tetrahydro-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 2730-02-1 1,5-diphenyl-3-(trifluoromethyl)-1H-pyrazole 
• 97935-94-9 3-(4-Hydroxy-phenyl)-5-(4-methoxy-phenyl)-1-phenyl-1H-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 97936-06-6 3-(4-Hydroxy-phenyl)-1,5-diphenyl-tetrahydro-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 37097-17-9 14-(p-hydroxyphenyl)-14H-dibenzo[a,j]xanthene 
• 1448593-90-5 3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole-5-carbonitrile 
• 1448594-06-6 5-(4-hydroxyphenyl)-3-(3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-1,2,4-oxadiazole 
• 1448594-05-5 5-(3,4,5-trimethoxyphenyl)-3-(3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-1,2,4-oxadiazole 
• 1448594-04-4 5-(3,4-dimethoxyphenyl)-3-(3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-1,2,4-oxadiazole 
• 1448594-03-3 5-(4-chlorophenyl)-3-(3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-1,2,4-oxadiazole 
• 1448772-66-4 (Z)-N'-hydroxy-3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole-5-carboximidamide 

Relevant articles and documents

Efficient Method for Aromatic-Aldehyde Oxidation by Cleavage of Their Hydrazones Catalysed by Trimethylsilanolate

The reactions of hydrazones, derived from various aromatic aldehydes bound to Rink resin and hydrazines, with trimethylsilanolate have been studied. In this process, the aldehydes were oxidized to the corresponding carboxylic acids. The reaction was also tested with success in solution, with various aromatic aldehydes easily being oxidized in one pot via hydrazone formation and trimethylsilanolate treatment. A mechanism for the hydrazone cleavage is proposed. The reaction may be used as an alternative method for aldehyde oxidation with the selectivity complementary to that of currently used reactions.

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.

Synthesis of and characterization of some Heterocyclic Compounds derived from Thiophenol

This research work involved preparation of heterogeneous pent lateral cyclic compounds (thiazolidine -4- one, benzothiazole, triazole, 4-oxothiazolidin) using thiophenol as raw materials: Thiophenol was reacted with mono chloroacetic acid in the presence of potassium hydroxide to prepare (sh1) followed by ortho amino aniline results the (sh2). The reaction of thiophenol with ethylchloroacetate afforded (sh3) and the reaction of (sh3) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4- triazole (sh5). A treatment of thiophenol with hydrazine hydrate to obtain the intermediate (sh6) with aromatic aldehyde synthesized azomethines (sh7- sh9) then treated with mercaptoacetic acid to obtained (sh10-sh12). A treatment of thiophenol with chloroacetyl chloride produced (sh13) compound then treated with hydrazine hydrate to obtain (sh14) compound followed by bromobenzaldehyde synthesized azomethine (sh15) compound then treated with mercaptoacetic acid to obtained (sh16) compound. Characterization results for the prepared compounds using IR spectroscopy, NMR and melting points confirmed their chemical structures.

sp2-C–H Acetoxylation of Diversely Substituted (E)-1-(Arylmethylene)-2-phenylhydrazines Using PhI(OAc)2 as Acetoxy Source at Ambient Conditions

A catalyst- and additive-free simple and straightforward method for regioselective direct sp2 C–H acetoxylation reaction of aldehyde hydrazones has been achieved at ambient temperature employing PIDA as an acetoxy source. The scope of the reaction has been successfully verified with a wide range of biologically important aldehyde hydrazones with diverse functional group tolerance. The method is highly selective, mild and efficient, operationally simple, rapid and high-yielding.

Lewis acid–catalyzed green synthesis and biological studies of pyrrolo[3,4-c]pyrazoles in aqueous medium

An environmentally benign approach in aqueous medium by means of Lewis acid catalyst affords a wide spectrum of pyrazoline derivatives in satisfactory yields. [3+2] cycloaddition reactions of substituted azomethine-N-imines to maleimide in aqueous medium at relatively high concentrations of Lewis acid catalyst have emerged as an environment friendly alternative to conventional solvents. Promising catalytic activity has been revealed by Lewis acid like Cu (NO3)2 in aqueous medium. The obvious features of this synthetic protocol were short reaction time, high efficiency, less hazardous synthesis by benign solvent, catalysis, modest workup, and a clean reaction methodology.

Fe+3-montmorillonite K10 as an Efficient Reusable Heterogeneous Catalyst for the Grind Mediated Synthesis of 14-aryl-14H-dibenzo [a,j]xanthenes

Background: Xanthenes are an important class of organic compounds and have also received significant attention due to their wide range of pharmacological activities such as antibacterial, antiviral, antiinflammatory activities, antagonists for the paralyzing action of zoxazolamine and efficiency in photodynamic therapy, a well-known method for controlling the localized tumors. Natural sources are also rich of xanthene compounds. Popularly known pigments, santalin have been isolated from plant species. Furthermore, these compounds can be emerged as pH-sensitive fluorescent materials for visualization of biomolecules, in laser technologies and as dyes. There are several reports in the literature for the synthesis of xanthenes such as alkylations of heteroatoms, cyclodehydrations, cyclocondensations between 2-hydroxyaromatic aldehydes and 2- tetralone, trapping of benzynes by phenols and intramolecular phenyl-carbonyl coupling reactions of benzaldehydes and acetophenones bearing tethered carbonyl chains in the presence of hexamethylphosphoramide and SmI2. Other methods for the synthesis of xanthenes include the reaction of formamide with β-naphthol, carbon monoxide, and 1- hydroxymethyl-naphthalen-2-ol. Methods: procedure a: A mixture of substituted benzaldehyde, 2-naphtol and Fe+3-montmorillonite K10 was mixed. After completion of the reaction, the product was solved in CHCl3 (3×10 mL) and insoluble catalyst was removed by filtration. The organic phase including the product and chloroform was evaporated under vacuum. The resulting crude material was purified by recrystallization from EtOH to afford pure products. procedure b: A mixture of substituted benzaldehyde, phenylhydrazine and Fe+3-montmorillonite K10 were added to a mortar and the mixture was pulverized with a pestle. After completion of the reaction, 2-naphtol was added to the consulting mixture and pulverized with a pestle. The organic phase including the product and chloroform was evaporated under vacuum. The resulting crude material was purified by recrystallization from EtOH to afford pure products. Results: As part of our going interest for the development of efficient and environmentally friendly procedures for the synthesis of heterocyclic and pharmaceutical compounds, we wish to report the first grind mediated synthesis of some derivatives of xanthenes using catalytic amount of Fe+3-montmotillonite. Conclusion: In conclusion, we have investigated the Fe+3-montmorillonite K10 under grinding as a mild and efficient catalyst for the synthesis of substituted 14-aryl-14H-dibenzo [a,j]xanthenes. The remarkable advantages offered by this method are: catalyst is inexpensive, non-toxic, easy handling and reusability, simple work-up procedure, short reaction time, high yields of product with better purity and green aspect by avoiding toxic catalyst and hazardous solvent.

Room temperature ionic liquid choline chloride-oxalic acid: A versatile catalyst for acid-catalyzed transformation in organic reactions

An efficient and facile synthesis of hydrazones, bis(indolyl)methanes and bis(4-hydroxycoumarin)methanes is facilitated by room temperature ionic liquid choline chloride-oxalic acid (ChCl:Ox). ChCl:Ox (10 mol%) efficiently catalyzes condensation of aldehydes with phenylhydrazine giving corresponding hydrazones in high yield (92-96%) within short reaction time of 3-5 min. Electrophilic cyclization reaction of indole and 4-hydroxy coumarin with aromatic aldehyde was effectively promoted by 30 mol% of ChCl:Ox giving corresponding bis(indolyl)arylmethanes and bis (4-hydroxycoumarin)methanes in good yield at room temperature. Procedure is very simple, solvent free and completely eliminates use of toxic acid catalyst. ChCl:Ox is biodegradable, can be recycled and reused without the loss of efficiency with respect to yield.

The enhanced efficiency to 3.6% based on organic dye as donor and Si/TiO2 acceptor bulk hetero-junction solar cells

The efficient organic dyes 2-{4-[2-(2-hydroxybenzylidene)hydrazino]phenyl} ethylene-1,1,2-tricarbonitrile and 2-{4-[2-(4-hydroxybenzylidene)hydrazino] phenyl}ethylene-1,1,2-tricarbonitrile have been synthesized, characterized and fabricated as hetero-junction solar cell materials. We use B3LYP/6-31G*, B3LYP/6-31G** and HF/6-31G** level of theories to optimize the ground state geometries. The absorption wavelengths have been computed by using time dependent density functional theory which is in good agreement with the experimental data. The hetero-junction solar cell devices have been fabricated by organic-inorganic heterojunction (dye/Si/TiO 2) and measured the efficiency by applying the incident power 30, 50 and 70 mW/cm2. The maximum efficiency 3.6% for dye2 has been observed. We shed light on the electronic and charge transport properties. Moreover, the stability and external quantum efficiencies have been measured.

Oxidized single-walled carbon nanotubes (swcns-cooh) as a new catalyst for the protection of carbonyl groups as hydrazones

Nano-materials are considered as suitable heterogeneous catalysts for many organic reactions. Herein oxidized carbon nanotube (SWCNTs-COOH) has been reported as a heterogeneous catalyst, for protection of carbonyl groups as hydrazones in EtOH at 80 C. The reactions proceed smoothly with good to excellent yields, and the SWCNTs-COOH used can be recycled.

Diaryl hydrazones as multifunctional inhibitors of amyloid self-assembly

The design and application of an effective, new class of multifunctional small molecule inhibitors of amyloid self-assembly are described. Several compounds based on the diaryl hydrazone scaffold were designed. Forty-four substituted derivatives of this core structure were synthesized using a variety of benzaldehydes and phenylhydrazines and characterized. The inhibitor candidates were evaluated in multiple assays, including the inhibition of amyloid β (Aβ) fibrillogenesis and oligomer formation and the reverse processes, the disassembly of preformed fibrils and oligomers. Because the structure of the hydrazone-based inhibitors mimics the redox features of the antioxidant resveratrol, the radical scavenging effect of the compounds was evaluated by colorimetric assays against 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals. The hydrazone scaffold was active in all of the different assays. The structure-activity relationship revealed that the substituents on the aromatic rings had a considerable effect on the overall activity of the compounds. The inhibitors showed strong activity in fibrillogenesis inhibition and disassembly, and even greater potency in the inhibition of oligomer formation and oligomer disassembly. Supporting the quantitative fluorometric and colorimetric assays, size exclusion chromatographic studies indicated that the best compounds practically eliminated or substantially inhibited the formation of soluble, aggregated Aβ species, as well. Atomic force microscopy was also applied to monitor the morphology of Aβ deposits. The compounds also possessed the predicted antioxidant properties; approximately 30% of the synthesized compounds showed a radical scavenging effect equal to or better than that of resveratrol or ascorbic acid.