280992
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:
Molecular Weight:
175.14
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
224-191-7
Beilstein/REAXYS Number:
141548
MDL number:
Assay:
97%
Form:
solid
InChI key
ISULLEUFOQSBGY-UHFFFAOYSA-N
InChI
1S/C8H5N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H
SMILES string
O=C1N=NC(=O)N1c2ccccc2
assay
97%
form
solid
mp
165-170 °C (dec.) (lit.)
storage temp.
2-8°C
Quality Level
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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:
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Rebecca L Grange et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(29), 8894-8903 (2010-06-24)
A detailed examination of [4+2] cycloaddition reactions between 1,8-disubstituted cyclooctatetraenes and diazo compounds revealed that 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) reacts to form either 2,3- or 3,4-disubstituted adducts. The product distribution can be controlled by modulating the electron density of the cyclooctatetraene. Unprecedented
4-Phenyl-1, 2, 4-triazoline-3, 5-dione: a novel dehydrogenating agent for dihydropyridazines
Klindert T and Seitz G
Synthetic Communications, 26(13), 2587-2596 (1996)
Fast Hetero-Diels- Alder Reactions Using 4-Phenyl-1, 2, 4-triazoline-3, 5-dione (PTAD) as the Dienophile
Celius TC
Journal of Chemical Education, 87(11), 1236-1237 (2010)
A reinvestigation of the reaction of allylsilanes with N-phenyltriazolinedione: stereoselective synthesis of substituted urazoles by [3+2] cycloaddition
Raudra T. Dey
Tetrahedron Letters, 48, 6671-6671 (2007)
Tatsuya Higashi et al.
Analytical and bioanalytical chemistry, 403(2), 495-502 (2012-03-01)
The utility of Diels-Alder derivatization with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) for liquid chromatography/electrospray ionization tandem mass spectrometry of conjugated linoleic acids (CLAs) was examined. PTAD rapidly reacted with the CLAs, and the resulting derivatives were highly responsive in electrospray ionization mass spectrometry
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