4233-33-4 Usage
Description
4-Phenyl-1,2,4-triazoline-3,5-dione, also known as Cookson reagent, is a strong dienophile that forms 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 and is characterized as a red solid.
Uses
Used in Analytical Chemistry:
4-Phenyl-1,2,4-triazoline-3,5-dione is 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.
Used in the Synthesis of Vitamin D3-Related Compounds:
4-Phenyl-1,2,4-triazoline-3,5-dione serves as a protecting group of the diene moiety in the synthesis of vitamin D3 (VD3)-related compounds.
Used in Organic Chemistry:
4-Phenyl-1,2,4-triazoline-3,5-dione is used as an efficient and selective reagent for the oxidation of thiols to disulfides.
Used in Pharmaceutical Industry:
4-Phenyl-1,2,4-triazoline-3,5-dione is used as a dehydrogenating agent to synthesize annulated dihydropyridazines by inverse [4+2] cycloaddition reaction between cyclic alkenes and 1,2,4,5-tetrazines.
Used in Chemical Synthesis:
4-Phenyl-1,2,4-triazoline-3,5-dione acts as a dienophile to synthesize cycloaddition products by fast hetero-Diels-Alder reactions.
Used in the Synthesis of Pyridine Derivatives:
4-Phenyl-1,2,4-triazoline-3,5-dione serves as an efficient oxidizing agent for the synthesis of pyridine derivatives from 1,4-dihydropyridines.
Used in the Synthesis of Urazoles:
4-Phenyl-1,2,4-triazoline-3,5-dione is used in the synthesis of urazoles via [3+2] cycloaddition with allylsilanes.
Synthesis Reference(s)
Synthetic Communications, 17, p. 409, 1987 DOI: 10.1080/00397918708063918
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 4233-33-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,2,3 and 3 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4233-33:
(6*4)+(5*2)+(4*3)+(3*3)+(2*3)+(1*3)=64
64 % 10 = 4
So 4233-33-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H5N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H
4233-33-4Relevant articles and documents
Oxidative dehydrogenation of 4-arylurazoles
Wamhoff,Zlotskii,Saprygina
, p. 332 - 332 (2002)
4-Arylurazoles are selectively oxidized with Fe2(NO 3)3·9H2O to the corresponding Δ1-1,2,4-triazoline-3,5-diones.
METHOD FOR PRODUCING SOLID TRIAZOLINEDIONE COMPOUND, SOLID TRIAZOLINEDIONE COMPOUND, AND METHOD FOR PRODUCING TRIAZOLINEDIONE COMPOUND
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Paragraph 0160-0163, (2020/12/25)
Provided are a method for separating a DAPTAD-containing triazolinedione compound in solid form from a reaction solution, a separated solid triazolinedione compound, and a novel method for producing a triazolinedione compound. A triazolinedione solution in which a DAPTAD-containing triazolinedione compound is dissolved is brought into contact with a C5-15 hydrocarbon-based poor solvent to obtain a solid triazolinedione compound. Also, a triazolinedione compound is oxidized using an oxidizing agent that does not produce acid as a byproduct to obtain a triazolinedione compound.
Melamine-(H2SO4)3/Melamine-(HNO3)3 Instead of H2SO4/HNO3: Benign System for Oxidation/Nitration Reactions from in situ NO2 +
Chehardoli, Gholamabbas,Azimi, Seyedeh Bahareh
, p. 589 - 594 (2019/11/16)
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[2π + 2π]-Cycloaddition of biadamantylidene to 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione. Effects of temperature, high pressure, and solvent
Kiselev,Kornilov,Anikin,Sedov,Konovalov
, p. 1864 - 1869 (2018/02/06)
The effects of temperature, solvent nature, and high hydrostatic pressure on the rate of the reaction of biadamantylidene with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione have been estimated. Significant shielding of the C=C double bond in biadamantylidene is responsible for the high entropy and volume of activation. Quantitative yield of the reaction in the temperature range 25?45°C is related to its exothermicity. The rate of the [2π + 2π]-cycloaddition unexpectedly weakly depends on the solvent polarity, which makes it radically different from the [2π + 2π]-reaction with tetracyanoethylene.