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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:
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 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’.

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Cycloheptatriene 95%

Sigma-Aldrich

C99205

Cycloheptatriene

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)
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
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
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)
Location of conjugated diene position in an aliphatic chain by mass spectrometry of the 4-phenyl-1,2,4-triazoline-3,5-dione adduct.
D C Young et al.
Analytical chemistry, 59(15), 1954-1957 (1987-08-01)
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