4-Phenylurazole Property

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

Safety Statements 

22-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29339990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Phenylurazole Chemical Properties,Usage,Production

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&region=US&gclid=EAIaIQobChMI6r7k0eu71gIV1IZoCh0nwgLjEAAYASAAEgI0tvD_BwE
http://nopr.niscair.res.in/handle/123456789/21799