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188956 Sigma-Aldrich

4-Phenylurazole

98%

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

  • CAS Number 15988-11-1

  • Empirical Formula (Hill Notation) C8H7N3O2

  • Molecular Weight 177.16

  •  Beilstein/REAXYS Number 163361

  •  EC Number 240-127-0

  •  MDL number MFCD00005226

  •  PubChem Substance ID 24851358

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Properties

Related Categories Building Blocks, Chemical Synthesis, Heterocyclic Building Blocks, Triazoles
InChI Key   GOSUFRDROXZXLN-UHFFFAOYSA-N
assay   98%
mp   207-209 °C (lit.)

Description

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.

Packaging

25 g in glass bottle

Other Notes

Electrochemically Promoted Tyrosine-Click-Chemistry for Protein Labeling

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles
Peer-Reviewed Papers
15

References

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