ChemicalBook CAS DataBase List 4233-33-4

4233-33-4

Name	4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE
CAS	4233-33-4
EINECS(EC#)	224-191-7
Molecular Formula	C8H5N3O2
MDL Number	MFCD00003148
Molecular Weight	175.14
MOL File	4233-33-4.mol

Chemical Properties

Melting point	165-170 °C (dec.)(lit.)
Boiling point	263.8±23.0 °C(Predicted)
density	1.47±0.1 g/cm3(Predicted)
storage temp.	2-8°C
pka	-1.71±0.20(Predicted)
BRN	141548
InChIKey	ISULLEUFOQSBGY-UHFFFAOYSA-N
CAS DataBase Reference	4233-33-4(CAS DataBase Reference)

Safety Data

Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	3
HS Code	29339900

Hazard Information

Chemical Properties

4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE is Red Solid

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-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.

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.

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.

Synthesis Reference(s)

Synthetic Communications, 17, p. 409, 1987 DOI: 10.1080/00397918708063918

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.

Purification Methods

PTAD forms carmine red needles by sublimation (ice cold finger) at 100o/0.1mm, and/or by recrystallisation from EtOH. IR: 1760 and 1780 cm-1 . [Cookson et al. Org Synth 51 121 1971, Moore max et al. J Org Chem 39 3700 1974, Beilstein 26 I 57, 26 III/IV 540.]

Spectrum Detail

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