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:

99% ^*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-(1,1-dimethyl-2,3-dihydro-1H-silol-3-yl)-4-phenyl-[1,2,4]triazolidine-3,5-dione

2,6-diphenyl-1H,5H-<1,2,4>triazolo<1,2-a><1,2,4>triazole-1,3,5,7(2H,6H)-tetrone

4-phenyl-1-(tetrahydro-2-furanyl)-1,2,4-triazolidine-3,5-dione

1-(2-methyl-3-indolyl)-4-phenylurazole

Refernces

• 1、 Mehta, Goverdhan,Uma. "Role of Heteroatoms in Diastereofacial Control in Cycloaddition to a Dissymmetric Cyclohexa-1,3-diene Moiety in a Polycyclic Framework. Remarkable Stereodirecting Influence of Distal Protective Groups". . p. 1685 - 1696. Retrieved 2000.
• 2、 -. "Diazacyclobutene derivatives and methods of synthesis thereof". Page/Page column 12. . Retrieved 2021/01/17.
• 3、 Yoshidomi, Shohei,Abe, Manabu. "1,2-Diazacyclopentane-3,5-diyl Diradicals: Electronic Structure and Reactivity". supporting information. p. 3920 - 3933. Retrieved 2019/03/07.