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Merck
CN
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文件

280992

Sigma-Aldrich

4-苯基-1,2,4-三唑啉-3,5-二酮

97%

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别名:
4-苯基-3H-1,2,4-三唑-3,5(4H)-二酮, PTAD
经验公式（希尔记法）:
C8H5N3O2
CAS号:
4233-33-4
分子量:
175.14
Beilstein:
141548
EC 号:
224-191-7
MDL编号:
MFCD00003148
UNSPSC代码:
12352005
PubChem化学物质编号:
24856961
NACRES:
NA.22

质量水平

100

检测方案

97%

形式

solid

mp

165-170 °C (dec.) (lit.)

储存温度

2-8°C

SMILES字符串

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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应用

4-苯基-1,2,4-三唑啉-3,5-二酮(PTAD)可用作将硫醇氧化成二硫化物的高效选择性试剂。
它还用于：       
  • 作为环烯烃和1,2,4,5-四嗪通过逆[4+2]环加成反应合成二氢哒嗪环的脱氢剂。       
  • 作为快速杂-Diels-Alder反应合成环加成产物的亲双烯体。       
  • 作为1,4-二氢吡啶类物质合成吡啶衍生物的高效氧化剂。
  • 作为烯丙基硅烷[3+2]环加成合成尿唑的试剂。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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-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
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
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
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