188956
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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
240-127-0
Beilstein/REAXYS Number:
163361
MDL number:
Assay:
98%
Product Name
4-Phenylurazole, 98%
InChI key
GOSUFRDROXZXLN-UHFFFAOYSA-N
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)
SMILES string
O=C1NNC(=O)N1c2ccccc2
assay
98%
mp
207-209 °C (lit.)
Quality Level
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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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
Chemische Berichte, 121, 185-185 (1988)
Synthesis of aliphatic polyamides containing 4-phenylurazole linkages.
Mallakpour SE and Sheikholeslami B.
Polymer International, 48(1), 41-46 (1999)
Bulletin of the Chemical Society of Japan, 61, 3915-3915 (1988)
Journal of the American Chemical Society, 109, 3730-3730 (1987)
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