Basic information Safety Supplier Related

4-Phenylurazole

Basic information Safety Supplier Related

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
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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
pka
5.43±0.30(Predicted)
form 
powder to crystal
color 
White to Almost white
BRN 
163361
InChIKey
GOSUFRDROXZXLN-UHFFFAOYSA-N
CAS DataBase Reference
15988-11-1(CAS DataBase Reference)
NIST Chemistry Reference
4-Phenylurazole(15988-11-1)
EPA Substance Registry System
1,2,4-Triazolidine-3,5-dione, 4-phenyl- (15988-11-1)
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
TSCA 
Yes
HS Code 
29339990

MSDS

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4-Phenylurazole Usage And Synthesis

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&region=US&gclid=EAIaIQobChMI6r7k0eu71gIV1IZoCh0nwgLjEAAYASAAEgI0tvD_BwE
http://nopr.niscair.res.in/handle/123456789/21799

4-Phenylurazole Preparation Products And Raw materials

Raw materials

4-PhenylurazoleSupplier

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