15988-11-1

Basic information

• Product Name: 4-Phenylurazole
• Synonyms: AURORA KA-3647;4-PHENYLTETRAHYDRO-1,2,4-TRIAZOLE-3,5-DIONE;4-PHENYLURAZOLE;4-PHENYL-1,2,4-TRIAZOLANE-3,5-DIONE;4-PHENYL-1,2,4-TRIAZOLIDINE-3,5-DIONE;1,2,4-Triazolidine-3,5-dione, 4-phenyl-;1,2,4-Triazolidine-3,5-dione,4-phenyl-;2,4-Triazolidine-3,5-dione,4-phenyl-1
• CAS NO: 15988-11-1
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.16
• EINECS: 240-127-0
• Product Categories: Naphthyridine,Quinoline;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Triazoles
• Mol File: 15988-11-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 207-209 °C(lit.)
• Boiling Point: 309.07°C (rough estimate)
• Appearance: white to light beige cryst. powder or granules
• Density: 1.3393 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 5.43±0.30(Predicted)
• BRN: 163361
• CAS DataBase Reference: 4-Phenylurazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylurazole(15988-11-1)
• EPA Substance Registry System: 4-Phenylurazole(15988-11-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 15988-11-1(Hazardous Substances Data)

Usage

Description

4-phenylurazole is a kind of laboratory chemicals used for the manufacturing of some substances. It can be used as the precursor to the Diels-Alder trapping agent, 4-phenyl-1, 2, 4-triazoline-3, 5-Dione. Its derivative, azo dyes, has wide applications in dyes industry. In the presence of phosgene, terephthaloyl chloride and epichlorohydrin, it can be polymerized to yield insoluble polymer.

Chemical Properties

white to light beige cryst. powder or granules

Uses

Precursor to the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione.1,2,3

General Description

4-Phenylurazole undergoes oxidation in the presence of NO2-N2O4 to yield 4-phenyl-1,2,4-trizoline-3,5-dione. It undergoes acetylation reaction with excess acetyl chloride in N,N-dimethylacetamide solution. It polymerizes in the presence of phosgene, terephthaloyl chloride and epichlorohydrin to yield insoluble polymer. It is precursor to the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione. This urazole was recently demonstrated in the traceless, chemoselective labeling of peptides and proteins through electrochemical tyrosine-click (e-Y-CLICK) chemistry.

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

• 58386-20-2 2,5-bismethoxythiophene 
• 79532-62-0 1-(1-Ethoxy-2-oxocyclohexyl)-4-phenyl-1,2,4-triazolidin-3,5-dion 
• 110-21-4 hydrazodicarboxamide 
• 142-04-1 aniline hydrochloride 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 613-91-2 acetophenone oxime 
• 629-31-2 1-heptanal oxime 
• 100-64-1 cyclohexanone-oxime 
• 127-06-0 acetone oxime 
• 17102-64-6 Sorbyl alcohol 
• 50-81-7 ascorbic acid 
• 103-71-9 phenyl isocyanate 
• 563-41-7 semicarbazide hydrochloride 
• 6320-72-5 4-nitrophenyl-N-phenyl carbamate 

Downstream Products

• 63412-64-6 1,2-dibenzoyl-4-phenyl-1,2,4-triazolidine-3,5-dione 
• 1010-53-3 3-phenyl-2,4-thiazolidinedione 
• 119020-75-6 3-phenyl-6-methoxycarbonyl-1,3,5-triazabicyclo[ 3.1.0]hexane-2,4-dione 
• 1263379-94-7 9-(4-isopropylphenyl)-6,6-dimethyl-2-phenyl-6,7-dihydro-[1,2,4]triazolo[1,2-a]indazole-1,3,8(2H,5H,9H)-trione 
• 1263380-07-9 6,6-dimethyl-2-phenyl-6,7-dihydro-1H,2'H-spiro[[1,2,4]triazolo[1,2-a]indazole-9,1'-acenaphthylene]-1,2',3,8(2H,5H)-tetraone 
• 1263379-96-9 4-(6,6-dimethyl-1,3,8-trioxo-2-phenyl-1,2,3,5,6,7,8,9-octahydro-[1,2,4]triazolo[1,2-a]indazol-9-yl)benzonitrile 
• 1263379-97-0 9-(3-methoxyphenyl)-6,6-dimethyl-2-phenyl-6,7-dihydro-[1,2,4]triazolo[1,2-a]indazole-1,3,8(2H,5H,9H)-trione 
• 1263379-98-1 6,6-dimethyl-9-(naphthalen-2-yl)-2-phenyl-6,7-dihydro-[1,2,4]triazolo[1,2-a]indazole-1,3,8(2H,5H,9H)-trione 
• 1263379-99-2 9,9'-(1,4-phenylene)bis(6,6-dimethyl-2-phenyl-6,7-dihydro-[1,2,4]triazolo[1,2-a]indazole-1,3,8(2H,5H,9H)-trione) 
• 1263380-04-6 5'-bromo-6,6-dimethyl-2-phenyl-6,7-dihydro-1H-spiro[[1,2,4]triazolo[1,2-a]indazole-9,3'-indoline]-1,2',3,8(2H,5H)-tetraone 
• 1263380-02-4 6,6-dimethyl-2-phenyl-6,7-dihydro-1H-spiro[[1,2,4]triazolo[1,2-a]indazole-9,3'-indoline]-1,2',3,8(2H,5H)-tetraone 
• 1263380-03-5 5'-fluoro-6,6-dimethyl-2-phenyl-6,7-dihydro-1H-spiro[[1,2,4]triazolo[1,2-a]indazole-9,3'-indoline]-1,2',3,8(2H,5H)-tetraone 
• 1234426-78-8 3-pyrrolidin-1-yl-6-phenyl-1,1,5,7-tetraoxo-1λ6-[1,2,4]triazolo[1,2-b][1,2,3,5]thiatriazole 
• 1234426-76-6 3-diethylamino-6-phenyl-1,1,5,7-tetraoxo-1λ6-[1,2,4]triazolo[1,2-b][1,2,3,5]thiatriazole 

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 articles and documents

A reliable multi-kilogram preparation of 4-phenylurazole

-

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.

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.