4-Phenylurazole
4-Phenylurazole Basic information
- Product Name:
- 4-Phenylurazole
- Synonyms:
-
- AURORA KA-3647
- 4-PHENYLTETRAHYDRO-1,2,4-TRIAZOLE-3,5-DIONE
- 4-PHENYLURAZOLE
- 4-PHENYL-1,2,4-TRIAZOLANE-3,5-DIONE
- 4-PHENYL-1,2,4-TRIAZOLIDINE-3,5-DIONE
- 1,2,4-Triazolidine-3,5-dione, 4-phenyl-
- 1,2,4-Triazolidine-3,5-dione,4-phenyl-
- 2,4-Triazolidine-3,5-dione,4-phenyl-1
- CAS:
- 15988-11-1
- MF:
- C8H7N3O2
- MW:
- 177.16
- EINECS:
- 240-127-0
- Product Categories:
-
- Building Blocks
- Chemical Synthesis
- Naphthyridine,Quinoline
- Heterocyclic Building Blocks
- Triazoles
- Mol File:
- 15988-11-1.mol
4-Phenylurazole Chemical Properties
- 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
- pka
- 5.43±0.30(Predicted)
- form
- powder to crystal
- color
- White to Almost white
- BRN
- 163361
- InChIKey
- GOSUFRDROXZXLN-UHFFFAOYSA-N
- 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
- Safety Statements
- 22-24/25
- WGK Germany
- 3
- TSCA
- Yes
- HS Code
- 29339990
MSDS
- Language:English Provider:4-Phenyl-1,2,4-triazolidine-3,5-dione
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
4-Phenylurazole Usage And Synthesis
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
Uses
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®ion=US&gclid=EAIaIQobChMI6r7k0eu71gIV1IZoCh0nwgLjEAAYASAAEgI0tvD_BwE
http://nopr.niscair.res.in/handle/123456789/21799
4-Phenylurazole Preparation Products And Raw materials
Raw materials
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