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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:
4233-33-4
Molecular Weight:
175.14
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24856961
EC Number:
224-191-7
Beilstein/REAXYS Number:
141548
MDL number:
MFCD00003148

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Product Name

4-Phenyl-1,2,4-triazoline-3,5-dione, 97%

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

100

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Show Differences

1 of 4

This Item
A818032589388.01309
4-Phenyl-1,2,4-triazoline-3,5-dione 97%

Sigma-Aldrich

280992

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

4-Amino-4H-1,2,4-triazole ReagentPlus®, 99%

Sigma-Aldrich

A81803

4-Amino-4H-1,2,4-triazole

4-Methyl-4H-1,2,4-triazole-3-thiol 97%

Sigma-Aldrich

258938

4-Methyl-4H-1,2,4-triazole-3-thiol

4-Amino-1,2,4-triazole for synthesis

Sigma-Aldrich

8.01309

4-Amino-1,2,4-triazole

assay

97%

assay

99%

assay

97%

assay

-

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

200

mp

165-170 °C (dec.) (lit.)

mp

84-86 °C (lit.)

mp

165-169 °C (lit.)

mp

83-86 °C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

2-30°C

form

solid

form

crystals

form

solid

form

powder

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.[1]
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.[2]       
  • As a dienophile to synthesize cycloaddition products by fast hetero-Diels−Alder reactions.[3]       
  • As an efficient oxidizing agent for the synthesis of pyridine derivatives from 1,4-dihydropyridines.[4]
  • In the synthesis of urazoles via [3+2] cycloaddition with allylsilanes.[5]

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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Certificates of Analysis (COA)

Lot/Batch Number
0000391736
0000391736
0000263977
MKCR7944
MKCR0041

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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-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
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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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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