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188956

Sigma-Aldrich

4-Phenylurazole

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H7N3O2
CAS Number:
Molecular Weight:
177.16
Beilstein/REAXYS Number:
163361
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

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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.

Related product

Product No.
Description
Pricing

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)


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A new method for the oxidation of 4-phenylurazole to 4-phenyltriazolinedione.
Mallakpour SE.
Journal of Chemical Education, 69(3), 238-238 (1992)
Bulletin of the Chemical Society of Japan, 61, 3915-3915 (1988)
Synthesis of aliphatic polyamides containing 4-phenylurazole linkages.
Mallakpour SE and Sheikholeslami B.
Polymer International, 48(1), 41-46 (1999)
Journal of the American Chemical Society, 109, 3730-3730 (1987)
Polycondensation Reaction of 4-(4'-N-1, 8-Naphthalimidophenyl)-1, 2, 4-triazolidine-3, 5-dione with Aliphatic Diacid Chlorides.
Mallakpour S and Rafiee Z.
Iranian Polymer Journal, 13, 225-234 (2004)

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