4-Phenyl-1,2,4-triazoline-3,5-dione
PTAD · 4-Phenyl-1,2,4-triazole-3,5-dione · 4-PHENYL-3 · AURORA KA-3851 · Mosapride Impurity 24 · 4-Phenyl-1,2,3-triazoline-3,5-dione · 4-phenyl-1,2,4-triazole-3,5-quinone · 4-Phenyl-1,2,4-triazoline-3,5-dione
Identifiers & Physical Properties
| CAS No. | 4233-33-4 |
|---|---|
| Molecular formula | C8H5N3O2 |
| Average molar mass | 175.14 g/mol |
| Monoisotopic mass | 175.0381764 g/mol |
| SMILES | O=C1N=NC(=O)N1c1ccccc1 |
| InChIKey | ISULLEUFOQSBGY-UHFFFAOYSA-N |
| PubChem CID | 77913 |
| ChEMBL | CHEMBL1354682 |
| EC No. | 224-191-7 |
| DTXSID | DTXSID00195142 |
Chemical & Physical Properties
| XLogP | 1.8 |
|---|---|
| Topological polar surface area | 62.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 251 |
| Solubility | 11.9 [ug/mL] (The mean of the results at pH 7.4)Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| Melting point | 165-170 °C (dec.)(lit.) |
| Boiling point | 263.8±23.0 °C(Predicted) |
| Density | 1.47±0.1 g/cm3(Predicted) |
| Storage conditions | 2-8°C |
| pKa (acidity coefficient) | -1.71±0.20(Predicted) |
| Physical state | Solid |
| Color | Red to Dark Red |
| BRN | 141548 |
| InChI | InChI=1S/C8H5N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H |
| InChIKey | ISULLEUFOQSBGY-UHFFFAOYSA-N |
| SMILES | N1C(=O)N(C2=CC=CC=C2)C(=O)N=1 |
| CAS DataBase Reference | 4233-33-4(CAS DataBase Reference) |
| FDA UNII | V3X3G4TFG6 |
| UNSPSC Code | 41116105 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P280-P305+P351+P338 |
| Safety statements (S) | 22-24/25 |
| Water hazard class (WGK) | 3 |
| Customs code | 29339900 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| Regulatory information | 3H-1,2,4-Triazole-3,5(4H)-dione, 4-phenyl-: Does not have an individual approval but may be used under an appropriate group standard |
|---|---|
| Water hazard class (WGK) | 3 |
| Customs code | 29339900 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Safety statements (S) | 22-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302 |
| GHS precautionary statements | P280-P305+P351+P338 |
Applications & Uses
Uses
4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) can be used as an efficient and selective reagent for the oxidation of thiols to disulfides.It can also be used:As a dehydrogenating agent to synthesize annulated dihydropyridazines by inverse [4+2] cycloaddition reaction between cyclic alkenes and 1,2,4,5-tetrazines.As a dienophile to synthesize cycloaddition products by fast hetero-DielsAlder reactions.As an efficient oxidizing agent for the synthesis of pyridine derivatives from 1,4-dihydropyridines.In the synthesis of urazoles via [3+2] cycloaddition with allylsilanes.
Uses
4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE is used in the methods for determining levels of 1,25 dihydroxyvitamin d2 and d3 in biological and food samples and dietary supplements.
Uses
4-Phenyl-1,2,4-triazoline-3,5-dione may be used as a derivatizing reagent for the determination of trace levels of 25-hydroxyvitamin D and its C-3 epimer in biological samples and cholecalciferol (vitamin D3) in fortified infant formula, milk and milk powder using liquid chromatography–tandem mass spectrometry (LC–MS/MS)technique.
General Description
4-Phenyl-1,2,4-triazoline-3,5-dione, also known as Cookson reagent, is a strong dienophile, which gives a stable Diels-Alder adduct quantitatively within a short time and under mild conditions. It is commonly used as a protecting group of the diene moiety for the synthesis of vitamin D3 (VD3)-related compounds.