Physicochemical Properties
| Molecular Formula | C8H5N3O2 |
| Molecular Weight | 175.14 |
| CAS # | 4233-33-4 |
| PubChem CID | 77913 |
| Appearance | Orange to red solid powder |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 263.8±23.0 °C at 760 mmHg |
| Melting Point | 165-170 °C (dec.)(lit.) |
| Flash Point | 113.3±22.6 °C |
| Vapour Pressure | 0.0±0.5 mmHg at 25°C |
| Index of Refraction | 1.701 |
| LogP | -0.25 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 13 |
| Complexity | 251 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1=CC=C(C=C1)N2C(=O)N=NC2=O |
| Synonyms | 4-Phenyl-1,2,4-triazoline-3,5-dione; 4233-33-4; 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione; PTAD; V3X3G4TFG6; NSC-150362; 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione; DTXSID00195142; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Biochemical assay reagent |
| ln Vitro | PTAD is exclusively used as a dienophile reagent in the Diels-Alder cycloaddition reaction for synthesizing dearomatized boronic ester intermediates. The study focuses on computational analysis of reaction mechanisms (diastereoselective 4+2 cycloaddition and 1,3-borotopic shift), utilizing distortion energy calculations to explain reactivity and stereoselectivity. No pharmacological or toxicological properties are investigated. [1] |
| References |
[1]. Computational assessments of diastereoselective 4+2 cycloaddition and 1,3-borotopic shift of a dearomatized tertiary boronic ester intermediate: reactivities explained through transition-state distortion energies. RSC Adv. 2019 Jul 26;9(40):23148-23155. |
| Additional Infomation | Interception of a dearomatized tertiary boronic ester, formed through a kinetically and thermodynamically favorable 1,2-metalate rearrangement/anti-SN2' elimination of an activated ortho-lithiated benzyl amine, in a [4+2] cycloaddition or 1,3-borotopic shift has been investigated by density functional theory (DFT). Although superacitvated "naked" Li+ was found to greatly promote 1,3-borotopic shift, the diastereoselective [4+2] cycloaddition was favored. It was revealed that the factor that controls the diastereoselectivity was the steric bulk provided by the diene, which is in agreement with experimental diastereoselectivity. A comparison of unreactive dienophiles such as maleic anhydride, diethyl maleate, and others with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD) was found to be in an excellent agreement with the experiments; where their lack of reactivity is attributed to the high deformation energies of the interacting components to achieve the transition state structure which was pronounced with the high energy of LUMO orbitals.[1] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.7097 mL | 28.5486 mL | 57.0972 mL | |
| 5 mM | 1.1419 mL | 5.7097 mL | 11.4194 mL | |
| 10 mM | 0.5710 mL | 2.8549 mL | 5.7097 mL |