4-Phenylurazole

4-Phenylurazole
  • CAS No.:15988-11-1
Other grades of this product :
4-Phenylurazole 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:15988-11-1
MF:C8H7N3O2
MW:177.16
EINECS:240-127-0
Product Categories:Building Blocks;Chemical Synthesis;Naphthyridine,Quinoline;Heterocyclic Building Blocks;Triazoles
Mol File:15988-11-1.mol
4-Phenylurazole Chemical Properties
Melting point 207-209 °C (lit.)
Boiling point 309.07°C (rough estimate)
density 1.3393 (rough estimate)
refractive index 1.6500 (estimate)
storage temp. Inert atmosphere,2-8°C
form powder to crystal
pka5.43±0.30(Predicted)
color White to Almost white
BRN 163361
InChIKeyGOSUFRDROXZXLN-UHFFFAOYSA-N
CAS DataBase Reference15988-11-1(CAS DataBase Reference)
NIST Chemistry Reference4-Phenylurazole(15988-11-1)
EPA Substance Registry System1,2,4-Triazolidine-3,5-dione, 4-phenyl- (15988-11-1)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
TSCA Yes
HS Code 29339990
MSDS Information
ProviderLanguage
4-Phenyl-1,2,4-triazolidine-3,5-dione English
SigmaAldrich English
ACROS English
ALFA English
4-Phenylurazole Usage And Synthesis
Description4-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 Propertieswhite to light beige cryst. powder or granules
UsesPrecursor to the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione.1,2,3
General Description4-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 MethodsCrystallise 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.]
Referenceshttp://www.sigmaaldrich.com/catalog/product/aldrich/188956?lang=en&region=US&gclid=EAIaIQobChMI6r7k0eu71gIV1IZoCh0nwgLjEAAYASAAEgI0tvD_BwE http://nopr.niscair.res.in/handle/123456789/21799
4-Phenylurazole Preparation Products And Raw materials
Raw materialsPotassium hydroxide solution-->Diethyl carbonate-->Phenyl isocyanate-->Semicarbazide-->4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE

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