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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

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About This Item

Empirical Formula (Hill Notation):
C8H5N3O2
CAS Number:
4233-33-4
Molecular Weight:
175.14
Beilstein/REAXYS Number:
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

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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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’.

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Sigma-Aldrich

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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
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
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
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
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