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4-Phenyl-1,2,4-triazoline-3,5-dione (CAS 4233-33-4)

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Alternate Names:
PTAD; 4-Phenyldehydrourazole
CAS Number:
4233-33-4
Molecular Weight:
175.14
Molecular Formula:
C8H5N3O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Phenyl-1,2,4-triazoline-3,5-dione (PTD) is a notable heterocyclic compound classified under the triazolinedione family. It holds significant importance as an intermediate in the synthesis of various organic compounds and finds widespread utilization in the creation organic products. The versatility of 4-Phenyl-1,2,4-triazoline-3,5-dione as a reagent is showcased by its application in diverse reactions, including the synthesis of polymers, polysaccharides, polyesters, polyphosphazenes, and polyamides. As a pivotal component in numerous organic synthesis methods, 4-Phenyl-1,2,4-triazoline-3,5-dione entices researchers and industries with its distinctive properties, rendering it an appealing and adaptable reagent.Similarly, agrochemical production benefits from incorporating 4-Phenyl-1,2,4-triazoline-3,5-dione in the creation of herbicides, insecticides, and fungicides. While the precise mechanism of action of 4-Phenyl-1,2,4-triazoline-3,5-dione remains unclear, it is widely believed to involve the formation of a conjugated system of electrons. This conjugated system arises from the reaction between the heterocyclic ring of 4-Phenyl-1,2,4-triazoline-3,5-dione and an electron-rich species like an amine or an ester. This reaction is postulated to generate a reactive intermediate, thereby enabling a diverse array of reactions, including addition, substitution, and elimination reactions.


4-Phenyl-1,2,4-triazoline-3,5-dione (CAS 4233-33-4) References

  1. Trapping of benzene oxide-oxepin and methyl-substituted derivatives with 4-phenyl- and 4-pentafluorophenyl-1,2,4-triazoline-3,5-dione.  |  Henderson, AP., et al. 2002. Chem Commun (Camb). 1956-7. PMID: 12271692
  2. Oxa-ene reaction of enols of amides with 4-phenyl-1,2,4-triazoline-3,5-dione.  |  Basheer, A. and Rappoport, Z. 2008. J Org Chem. 73: 184-90. PMID: 18072789
  3. Liquid chromatography-tandem mass spectrometric method for the determination of salivary 25-hydroxyvitamin D3: a noninvasive tool for the assessment of vitamin D status.  |  Higashi, T., et al. 2008. Anal Bioanal Chem. 391: 229-38. PMID: 18087693
  4. Polar hetero-Diels-Alder reactions of 4-alkenylthiazoles with 1,2,4-triazoline-3,5-diones: an experimental and computational study.  |  Alajarín, M., et al. 2008. J Org Chem. 73: 963-73. PMID: 18173287
  5. Fused polycyclic compounds via cycloaddition of 4-(1'-cyclohexenyl)-5-iodo-1,2,3-triazoles with 4-phenyl-1,2,4-triazoline-3,5-dione: the importance of a sacrificial iodide leaving group.  |  Michaels, HA., et al. 2013. J Org Chem. 78: 5038-44. PMID: 23621085
  6. LC-MS/MS for Identifying Patients with CYP24A1 Mutations.  |  Ketha, H., et al. 2016. Clin Chem. 62: 236-42. PMID: 26585929
  7. Accessing the Rare Diazacyclobutene Motif.  |  Narangoda, CJ., et al. 2018. Org Lett. 20: 8009-8013. PMID: 30525696
  8. Quantification of Alfacalcidol Tablets Dissolution Content by Chemical Derivatization and LC-MS.  |  Liu, Y., et al. 2020. J Anal Methods Chem. 2020: 6201656. PMID: 32089948
  9. Rolf Huisgen's Classic Studies of Cyclic Triene Diels-Alder Reactions Elaborated by Modern Computational Analysis.  |  Chen, PP., et al. 2020. Angew Chem Int Ed Engl. 59: 12506-12519. PMID: 32369676
  10. Donor-Acceptor Bicyclopropyls as 1,6-Zwitterionic Intermediates: Synthesis and Reactions with 4-Phenyl-1,2,4-triazoline-3,5-dione and Terminal Acetylenes.  |  Potapov, KV., et al. 2020. J Org Chem. 85: 15562-15576. PMID: 33175521
  11. Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for 'Photo-Clicked' Access to Carbamoyl Formazan Photoswitches In Situ.  |  Zheng, Y., et al. 2022. Chem Asian J. 17: e202101239. PMID: 34851039
  12. Location of conjugated diene position in an aliphatic chain by mass spectrometry of the 4-phenyl-1,2,4-triazoline-3,5-dione adduct.  |  Young, DC., et al. 1987. Anal Chem. 59: 1954-7. PMID: 3631517
  13. Synthesis of [3 alpha-3H]7-dehydrocholesterol via stable tritiated 4-phenyl-1,2,4-triazoline-3,5-dione derivative.  |  Batta, AK., et al. 1997. Steroids. 62: 700-2. PMID: 9366008
  14. Effector-sensitive cross-linking of phosphorylase b kinase by the novel cross-linker 4-phenyl-1,2,4-triazoline-3,5-dione.  |  Ayers, NA., et al. 1998. Biochem J. 331 (Pt 1): 137-41. PMID: 9512471

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

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

sc-252194
1 g
$113.00

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

sc-252194A
5 g
$324.00

4-Phenyl-1,2,4-triazoline-3,5-dione, 10 g

sc-252194B
10 g
$617.00

4-Phenyl-1,2,4-triazoline-3,5-dione, 100 g

sc-252194C
100 g
$5105.00

4-Phenyl-1,2,4-triazoline-3,5-dione, 500 g

sc-252194D
500 g
$20405.00