Skip to Content
Merck
All Photos(3)

Documents

280992

Sigma-Aldrich

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

97%

Synonym(s):

4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione, PTAD

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C8H5N3O2
CAS Number:
4233-33-4
Molecular Weight:
175.14
Beilstein:
141548
EC Number:
224-191-7
MDL number:
MFCD00003148
UNSPSC Code:
12352005
PubChem Substance ID:
24856961
NACRES:
NA.22

Assay

97%

form

solid

mp

165-170 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

O=C1N=NC(=O)N1c2ccccc2

InChI

1S/C8H5N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H

InChI key

ISULLEUFOQSBGY-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

K Søndergaard et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 7(11), 2324-2331 (2001-07-12)
The 5-aza-6-deoxy analogue of castanospermine (+/-)-5a and its 1-epimer (+/-)-5b was synthesized. The synthesis started from the known compound 5-benzyloxy-7-hydroxyhepta-1,3-diene, which was protected and subjected to Diels-Alder reaction with 4-phenyl-1,2,4-triazoline-3,5-dione to give two epimeric adducts. One of these was transformed
4-Phenyl-1, 2, 4-triazole-3, 5-dione as a novel and reusable reagent for the aromatization of 1, 4-dihydropyridines under mild conditions
Zolfigol MA, et al.
Tetrahedron Letters, 46(33), 5581-5584 (2005)
Ahmad Basheer et al.
The Journal of organic chemistry, 73(1), 184-190 (2007-12-13)
The reaction of 16 enols of amides with 4-phenyl-1,2,4-triazoline-1,3-dione gave open chain adducts rather than the [2 + 2] cycloadducts with a hemiaminal moiety, both in solid state and in solution. This assignment is based on X-ray crystallography, (1)H and
B Yeung et al.
Biochemical pharmacology, 49(8), 1099-1710 (1995-04-18)
1,25-Dihydroxy-16-ene vitamin D3 is a synthetic analog of 1,25-dihydroxyvitamin D3, the most physiologically active metabolite of vitamin D3. The renal metabolism of 1,25-dihydroxy-16-ene vitamin D3 had been studied previously using a perfused rat kidney system [Reddy et al., Bioorg Med
Darryl Eyles et al.
Clinica chimica acta; international journal of clinical chemistry, 403(1-2), 145-151 (2009-02-24)
Low levels of 25 hydroxyvitamin D (25OHD) during early development is associated with a range of adverse health outcomes. While a number of methods exist to measure 25OHD in sera, none have been specifically developed to examine dried blood spots
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service