15988-11-1

Usage

Uses

Used in Chemical Synthesis:
4-Phenylurazole is used as a precursor for the synthesis of the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione, which is an important intermediate in the production of various chemical compounds.
Used in Dyes Industry:
The derivative of 4-Phenylurazole, azo dyes, has wide applications in the dyes industry due to their diverse color properties and versatility in use.
Used in Polymer Synthesis:
4-Phenylurazole is used as a monomer in the polymerization process, yielding insoluble polymers when reacted with phosgene, terephthaloyl chloride, and epichlorohydrin. These polymers can be utilized in various applications, such as coatings, adhesives, and plastics.
Used in Pharmaceutical and Biotechnology Research:
4-Phenylurazole has been demonstrated in the traceless, chemoselective labeling of peptides and proteins through electrochemical tyrosine-click (e-Y-CLICK) chemistry, making it a valuable tool in pharmaceutical and biotechnology research for the development of new drugs and therapies.

Purification Methods

Crystallise 4-phenylurazole from water or 95% EtOH. Dissolve 35g in 80mL of boiling 95% EtOH and on cooling 90-95% is recovered with m 209-210o. It has IR with 1685 and 3120cm-1. [Cookson et al. Org max Synth 51 121 1971, Beilstein 26 I 64, 26 III/IV 540.]

References

http://www.sigmaaldrich.com/catalog/product/aldrich/188956?lang=en®ion=US&gclid=EAIaIQobChMI6r7k0eu71gIV1IZoCh0nwgLjEAAYASAAEgI0tvD_BwE http://nopr.niscair.res.in/handle/123456789/21799

InChI:InChI=1/C8H7N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H,(H,9,12)(H,10,13)

Upstream product

• 110-21-4 hydrazodicarboxamide 
• 142-04-1 aniline hydrochloride 
• 58386-20-2 2,5-bismethoxythiophene 
• 21922-69-0 4,4-dimethyl-3-piperidinocyclobut-2-en-1-one 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 79532-62-0 1-(1-Ethoxy-2-oxocyclohexyl)-4-phenyl-1,2,4-triazolidin-3,5-dion 
• 79532-63-1 1-(1-Ethoxy-3,7,7-trimethyl-2-oxo-bicyclo<2.2.1>heptyl)-4-phenyl-1,2,4-triazolidin-3,5-dion 
• 84040-26-6 4-Phenyl-1-(2,5,5-trimethoxy-2,5-dihydro-thiophen-2-yl)-[1,2,4]triazolidine-3,5-dione 
• 563-41-7 semicarbazide hydrochloride 
• 103-71-9 phenyl isocyanate 
• 64-17-5 ethanol 
• 613-91-2 acetophenone oxime 
• 629-31-2 1-heptanal oxime 
• 100-64-1 cyclohexanone-oxime 

Downstream Products

• 6598-92-1 9-Phenyl-8,10-dioxo-<4,1,7,9>thiatriazabicyclo<5.3.0>decan-4,4-dioxid 
• 42838-02-8 2,2,7-triphenyl-4,10-dihydro-[1,3]dioxolo[4,5-d][1,2,4]triazolo[1,2-a]pyridazine-6,8-dione 
• 61253-92-7 8-phenyl-1,5-dihydro-1,5-etheno-[1,2,4]triazolo[1,2-c][1,6,3,4]dioxadiazepine-7,9-dione 
• 60576-05-8 1,8a-Dihydro-N-phenylspiro<1,2-diazaazulen-3(2H),2'-<1,3>dithian>-1,2-dicarboximid 
• 63412-71-5 N,N'-(5,7-dioxo-6-phenyl-dihydro-[1,2,4]triazolo[1,2-c][1,3,4]thiadiazole-1,3-diylidene)-bis-carbamic acid diethyl ester 
• 94145-11-6 4-phenyl-1-<3-(1,2-benzodithiolio)>urazolide 
• 71366-11-5 10,10,11,11-Tetramethyl-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5-dion 
• 10316-54-8 4-phenyl-2,4,6-triazatricyclo[5.4.2.0^2,6]tridec-12-ene-3,5-dione 
• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 156304-65-3 1-(3,5-Di-tert-butyl2-hydroxy-1-phenyl)-4-phenyl-1,2,4-triazolidin-3,5-dion 
• 82204-55-5 C₁₅H₁₂ClN₃O₂ 
• 82204-57-7 C₁₅H₁₂ClN₃O₂ 
• 82204-56-6 C₁₅H₁₂ClN₃O₂ 
• 82204-58-8 5-chloro-N-phenyl-2,3-diazabicyclo<4.2.1>-nona-4,7-diene-2,3-dicarboximide 

Related news

Stabilization of 4-Phenylurazole (cas 15988-11-1) by electrografting on a nano-fibrillated mesoporous carbon modified electrode. Reactivity of anchored triazolinedione groups against Michael-type addition at electrode/electrolyte interface07/15/2019

Fabricartion of a redox-active electrode by modification of a glassy carbon electrode (GCE) with a unique ionic liquid derived fibrillated mesoporous carbon (IFMC) following the electrografting of 4-phenylurazole via electrochemical reduction of 4-(4-nitrophenyl)urazole in the presence of sodium...detailed

Unexpected formation of 5-alkylidene derivatives of hydantoin from the Michael addition of 4-Phenylurazole (cas 15988-11-1) to fumaric esters07/14/2019

An unexpected reaction between 4-phenylurazole and fumaric esters which led to the formation of 5-alkylidene derivatives of hydantoin is described in this paper. The reaction takes place in the presence of tetrabutylammonium bromide (TBAB), and 1,4-diaza-bicyclo[2,2,2]octane (DABCO) at 70 °C un...detailed

Relevant academic research and scientific papers

IMPROVED SYNTHESIS OF 4-ARYL-1,2,4-TRIAZOLIDINE-3,5-DIONES AND 4-ARYL-1,2,4-TRIAZOLINE-3,5-DIONES

The present invention relates to a method of preparing 4-aryl-1,2,4- triazolidine-3,5-dione of the formula (I) and 4-aryl-1,2,4-triazole-3,5-dione of the formula (VII). This method is particularly suitable as the synthesis of 4-aryl-1,2,4-triazolidine-3,5-dione of the formula (I) is made from the respective arylisocyanate of the formula (II) with a hydrazine carboxylate as a one pot reaction in an alcohol.

The reaction of oximes with 4-phenyl-1,2,4-triazoline-3,5-dione to produce nitric oxide – Model compounds for nitric oxide synthase

Certain oximes form nitric oxide upon reaction with 4-phenyl-1,2,4-triazole-3,5-dione (PTAD). The oximes appear to undergo an Alder-ene reaction with the PTAD enophile to form a nitroso intermediate capable of dimerization and/or nitric oxide formation. Upon exposure to oxygen, the nitroso compounds eventually form ketones. This reaction may serve as a model for the study of nitric oxide synthase (NOS), the enzyme responsible for physiological production of nitric oxide. NOS is known to produce an oxime intermediate which reacts with oxygen to produce nitric oxide and citrulline.

Tandem Functionalization in a Highly Branched Polymer with Layered Structure

A hyperbranched polymer with multilayer structure was developed to demonstrate the possibility of highly efficient tandem functionalization reactions at different domains within one nanostructured platform. The polymer scaffold was constructed by chain-growth copper-catalyzed azide–alkyne cycloaddition polymerization of three functional monomers with sequential monomer addition in one pot. Subsequent reactions with different monomer units resulted in efficient functionalization of each segment with construction of a highly sophisticated polymer structure by a robust procedure. As a proof of concept, the ability of this polymer structure to quantitatively load six species of guest molecules through three different types of conjugation reactions was demonstrated.

Reactions of 4-phenyl-1,2,4-triazoline-3,5-dione with 2-pyrazolines

4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) acts as an efficient Michael acceptor in reactions with 1-unsubstituted 2-pyrazolines, giving substituted (3,5-dioxo-4-phenyl-1,2,4-triazol-idin-1-yl)-1-pyrazolines in quantitative yields. Through elimination of molecular nitrogen, the latter are easily transformed into the corresponding cyclopropanes. A reaction of methyl 5-methyl-2-pyrazoline-5-carboxylate with a twofold excess of PTAD leads to an intermediate bisadduct, which undergoes dediazotization to form a 1,3,5-triazabicyclo[3.3.0]octane-2,4-dione derivative. 1-Substituted 2-pyrazolines also add to PTAD with the exception that the 2-pyrazoline structure is retained in the product because of the migration of the C(3)H proton to PTAD.

N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis. part IX.* novel triazolo-fused thiatriazoles and pyrazolo-fused oxathiazines

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with 4-substituted urazoles 2 to give [1,2,4]triazolo[1,2-b] [1,2,3,5]thiatriazoles 3 in a selective 1,2-NN dinucleophilic mode of reaction.The reaction of 1 with N1-substituted pyrazol-5-ones 4 afforded pyrazolo[4,3-e][1,4,3] oxathiazines 5 via selective 1,3-CCO dinucleophilic substitution. Compounds 3 and 5 were the sole products isolated from the respective reactions and both represent new ring systems. CSIRO 2010.

Azo bond hydrogenation with hydrazine, R-NHNH2, and hydrazobenzene

Hydrogenation of azo bonds with hydrazine, mono-substituted hydrazine, and hydrazobenzene was studied with selected diazene compounds under oxygen-free conditions. The reactions proceed rapidly and in high yield in several solvents, utilizing all N-H protons. While the reduction process is accompanied by the evolution of nitrogen gas in the case of N2H4, the intermediacy of diimide could not be confirmed by standard trapping experiments.

Novel and efficient synthesis of 4-substituted-1,2,4-triazolidine-3,5- diones from anilines

A simple and efficient three-step synthetic procedure for the preparation of 4-substituted phenyl derivatives of 1,2,4-triazolidindiones (urazoles), starting from anilines, has been developed. In this method, aniline derivatives were reacted with 4-nitrophenyl chloroformate to provide corresponding carbamate derivatives. In the second step, semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazate. The cyclization reaction of corresponding semicarbazides furnished 1,2,4-triazolidindiones in high yields. Copyright Taylor & Francis Group, LLC.

A novel one-pot synthesis of 4-substituted 1,2,4-triazolidine-3,5-diones

A simple and one-pot pathway for the preparation of 4-substituted phenyl derivatives of triazolidindiones (urazoles), starting from aniline derivatives is reported. In these methods aniline derivatives were reacted with ethyl chloroformate, to give the corresponding carbamate derivatives. In the second step semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazide. The cyclization reactions of the corresponding semicarbazides furnished triazolidindiones. All reactions were performed in one vessel without the isolation of reaction intermediates, such as carbamates and semicarbazides, and the final products were isolated in good yields. Georg Thieme Verlag Stuttgart.

N-Phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides

N-Phenyltriazolinedione is an efficient and chemoselective reagent for the oxidation of thiols to their corresponding symmetrical disulfides. The method is applicable to aromatic, aliphatic, and bi-functional thiols. The one-pot reaction takes a few minutes (in most cases studied) for completion and after a simple work-up affords the corresponding symmetrical disulfides in very good to excellent yields. Furthermore, the reaction could be performed with the same results in the absence of solvent for liquid thiols.