4-Phenylurazole (HCID 85229)

Names & identifiers

Preferred name: 4-Phenylurazole
IUPAC: 4-phenyl-1,2,4-triazolidine-3,5-dione
English name: 4-Phenylurazole
Molecular formula: C8H7N3O2
Molecular weight: 177.16

Names & synonyms

4-Phenylurazole15988-11-14-Phenyl-1,2,4-triazolidine-3,5-dione1,2,4-Triazolidine-3,5-dione, 4-phenyl-Bicarbamimide, N-phenyl-Urazole, 4-phenyl-9V4N9J1BIHEINECS 240-127-0NSC 93432DTXSID5065988NSC-93432GOSUFRDROXZXLN-UHFFFAOYSA-

Show more names

4-PhenylurazolAURORA KA-36474-phenyl urea yl4-Phenylurazole>4-PHENYLURAZOLE 99.0%4-Phenylurazole, 98+%Calcitriol Impurity 5

RefChem:526462DTXCID7035147240-127-0InChI=1/C8H7N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H,(H,9,12)(H,10,13)MFCD00005226SCHEMBL447261DS-24824-phenyl-1,2,4-triazolane-3,5-dione

Database identifiers

CAS: 15988-11-1
PubChem CID: 85229
DTXSID: DTXSID5065988
ChEMBL: CHEMBL224287
UNII: 9V4N9J1BIH
EC Number: 240-127-0
Nikkaji: J9.129D

Properties

Computed structural properties

XLogP: 0.7
Topological polar surface area: 61.4 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 13
Formal charge: 0
Complexity: 220

Experimental & physicochemical properties

Solubility17.2 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point: 207 · 207-209 °C (lit.)
Boiling point: 309.07 °C · 309.07°C (rough estimate)
Density: 1.3393 · 1.3393 (rough estimate)
refractive index: 1.65 · 1.6500 (estimate)
storage temp.: 2 · Inert atmosphere,2-8°C
pka: 5.43 · 5.43±0.30(Predicted)
form: powder to crystal
color: White to Almost white
BRN: 163361 · 163361
InChI: 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)
InChIKey: GOSUFRDROXZXLN-UHFFFAOYSA-N
SMILES: N1C(=O)N(C2=CC=CC=C2)C(=O)N1
CAS DataBase Reference: 15988 · 15988-11-1(CAS DataBase Reference)
FDA UNII: 9 V4N9J1BIH · 9V4N9J1BIH
NIST Chemistry Reference: 4 · 4-Phenylurazole(15988-11-1)
EPA Substance Registry System: 1 · 1,2,4-Triazolidine-3,5-dione, 4-phenyl- (15988-11-1)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H332-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29339990 · 29339990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory Information1,2,4-Triazolidine-3,5-dione, 4-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: TSCA listed
hs_code: 29339990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H332-H335
Precautionary statements: P261-P280-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing Information1,2,4-Triazolidine-3,5-dione, 4-phenyl-: ACTIVE

Applications · 3 items

Description4-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.

UsesPrecursor to the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione.1,2,3

General Description4-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.