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HomeProduct name list4-Phenylurazole

4-Phenylurazole

Synonym(s):4-Phenyl-1,2,4-triazolidine-3,5-dione;Ph-Ur for e-Y-CLICK

  • CAS NO.:15988-11-1
  • Empirical Formula: C8H7N3O2
  • Molecular Weight: 177.16
  • MDL number: MFCD00005226
  • EINECS: 240-127-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-04-27 16:27:43
4-Phenylurazole Structural

What is 4-Phenylurazole?

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

The Uses of 4-Phenylurazole

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

Properties of 4-Phenylurazole

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
pka 5.43±0.30(Predicted)
color  White to Almost white
BRN  163361
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)

Safety information for 4-Phenylurazole

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H332:Acute toxicity,inhalation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 4-Phenylurazole

InChIKey GOSUFRDROXZXLN-UHFFFAOYSA-N

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