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280992

Sigma-Aldrich

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

97%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C8H5N3O2
Número de CAS:
4233-33-4
Peso molecular:
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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «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)
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
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
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)
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
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