4-Phenyl-1,2,4-triazoline-3,5-dione

Base Information

• Chemical Name: 4-Phenyl-1,2,4-triazoline-3,5-dione
• CAS No.: 4233-33-4
• Molecular Formula: C8H5N3O2
• Molecular Weight: 175.147
• Hs Code.: 29339900
• European Community (EC) Number: 224-191-7
• NSC Number: 150362
• UNII: V3X3G4TFG6
• DSSTox Substance ID: DTXSID00195142
• Nikkaji Number: J205.659C
• Wikipedia: 4-Phenyl-1,2,4-triazole-3,5-dione
• Wikidata: Q905685
• ChEMBL ID: CHEMBL1354682
• Mol file: 4233-33-4.mol

Synonyms:4-phenyl-1,2,4-triazoline-3,5-dione;PTAD

Chemical Property of 4-Phenyl-1,2,4-triazoline-3,5-dione

Chemical Property:

• Vapor Pressure: 0.0101mmHg at 25°C
• Melting Point: 165-170 °C (dec.)(lit.)
• Refractive Index: 1.701
• Boiling Point: 263.812 °C at 760 mmHg
• PKA: -1.71±0.20(Predicted)
• Flash Point: 113.35 °C
• PSA: 62.10000
• Density: 1.471 g/cm³
• LogP: 1.13500
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Sli
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 175.038176411
• Heavy Atom Count: 13
• Complexity: 251

Purity/Quality:

97% ^*data from raw suppliers

4-Phenyl-1,2,3-triazoline-3,5-dione ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C(=O)N=NC2=O
• 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. 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-Diels?Alder 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. 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.

Technology Process of 4-Phenyl-1,2,4-triazoline-3,5-dione

There total 32 articles about 4-Phenyl-1,2,4-triazoline-3,5-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-Phenylurazole (15988-11-1) → 4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4)

Guidance literature:

With tetrabutylammonium periodite; In acetone; at 20 ℃; for 0.5h;

DOI:10.1021/jo070978f

Reference yield:

(1R,8S)-4,15-dimethyl-11-phenyl-9,11,13-triazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,14-tetraene-10,12-dione → 4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + 2.6-dimethylnaphthalene (581-42-0)

Guidance literature:

at 20 ℃; Equilibrium constant; Thermodynamic data; Kinetics; Activation energy;

DOI:10.1007/s11172-014-0506-x

Reference yield:

phenyl isocyanate (103-71-9) → 4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1: benzene / 20-25 deg C, 2 h; reflux, 2 h

2: KOH / H₂O / 2 h

3: anhydrous Na₂SO₄, N₂O₄ / CH₂Cl₂ / 0 °C

With dinitrogen tetraoxide; sodium sulfate; potassium hydroxide; In dichloromethane; water; benzene;

DOI:10.1021/ja00322a023

upstream raw materials:

4-Phenylurazole

10,11-Dimethylen-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5-dion

4-methyl-1,2,4-triazoline-3,5-dione

phenyl isocyanate

Downstream raw materials:

1-Methyl-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5,10-trion

(1S^*,10R^*)-10-Hydroxy-10-methyl-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5-dion

(1S^*,10S^*)-10-Hydroxy-10-methyl-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5-dion

3-(4-phenylurazolyl)-2-oxoindole

Refernces

3-Alkenyl-5-ferrocenyl-2-pyrazolines in reactions with azodicarboxylic acid N-phenylimide

10.1007/BF02494717

The research focuses on the chemical reactions of 3-alkenyl-5-ferrocenyl-2-pyrazolines with azodicarboxylic acid N-phenylimide. The study explores the [4+2]-cycloaddition mechanism to form Diels-Alder adducts and the monoene addition products when allylic hydrogen atoms are present. The reactants include 1-acetyl-3-(2-ferrocenylethenyl)-5-ferrocenyl-2-pyrazoline and azodicarboxylic acid N-phenylimide, with the synthesis of pyrazolines derived from ferrocenecarbaldehyde and acetone or 1-acetylcyclohexene. The analysis of the products involved elemental analysis, melting point determination, and NMR spectroscopy, including both proton (1H) and carbon (13C) NMR spectra, to establish the structures and confirm the presence of specific functional groups and the configuration of the molecules. The study aims to understand the chemical and pharmacological properties of these organic compounds, which are expected to exhibit enhanced biological activity and reduced toxicity due to the presence of ferrocene substituents.