188956

4-Phenylurazole

98%

• Synonym(s): 4-Phenyl-1,2,4-triazolidine-3,5-dione, Ph-Ur for e-Y-CLICK
• Empirical Formula (Hill Notation): C₈H₇N₃O₂
• CAS Number: 15988-11-1
• Molecular Weight: 177.16
• Beilstein/REAXYS Number: 163361
• EC Number: 240-127-0
• MDL number: MFCD00005226
• UNSPSC Code: 12352100
• PubChem Substance ID: 24851358
• NACRES: NA.22

Properties

• assay: 98%
• mp: 207-209 °C (lit.)
• SMILES string: O=C1NNC(=O)N1c2ccccc2
• InChI: 1S/C8H7N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H,(H,9,12)(H,10,13)
• InChI key: GOSUFRDROXZXLN-UHFFFAOYSA-N

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.

Other Notes

Electrochemically Promoted Tyrosine-Click-Chemistry for Protein Labeling

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)