CAS 15988-11-1|4-phenyl-1,2,4-triazolidine-3,5-dione|4-phenyl-1,2,4-triazolidine-3,5-dione|4-Phenylurazole 98%|4-苯基-1,2,4-三唑烷-3,5-二酮|4-Phenylurazole|4-苯基脲唑|4-Phenyl-1,2,4-triazolidine-3,5...

General Information

Structure

Molecular Formula

C₈H₇N₃O₂

Molecular Mass

177.16008

Exact Mass

177.05382648

Charge

InChI

InChI=1S/C8H7N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H,(H,9,12)(H,10,13)

InChIKey

GOSUFRDROXZXLN-UHFFFAOYSA-N

Canonic Smiles

O=c1[nH][nH]c(=O)n1c1ccccc1

Isomeric Smiles

n1(c2ccccc2)c(=O)[nH][nH]c1=O

Calculated Properties

JChem

Acid pKa

12.884686

H Acceptors

H Donor

LogD (pH = 5.5)

0.61370236

LogD (pH = 7.4)

0.6137011

Log P

0.61370236

Molar Refractivity

44.4595

Polarizability

16.87661

Polar Surface Area

61.44

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

4-phenyl-1,2,4-triazolidine-3,5-dione

IUPAC name

4-phenyl-1,2,4-triazolidine-3,5-dione

Synonyms

4-Phenylurazole 98%4-苯基-1,2,4-三唑烷-3,5-二酮4-Phenylurazole4-苯基脲唑4-Phenyl-1,2,4-triazolidine-3,5-dione4-Phenyl-1,2,4-triazolidine-3,5-dione

Names and Identifiers

Registration numbers

MDL Number

CAS Number

Beilstein Number

PubChem CID

EC Number

PubChem SID

Registration numbers

Properties

Product Information

Empirical Formula (Hill Notation)

C8H7N3O2

Purity

98%

98+%

Safety Information

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

是

Physical Property

207-209 °C(lit.)

206-210°C

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

188956

Packaging
5, 25 g in glass bottle
Application
Precursor to the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione.1,2,3

Molecule Details

References

PubChem Literature

From Data Sources

• ?-Diketones form adducts without an added catalyst. These yield 1,2,3-triketones on cleavage.

• 1,2,4-Triazolinediones form charge-transfer complexes with electron-rich aromatics, such as di- or trimethoxybenzenes: J. Org. Chem., 48, 1708 (1983).

• The adducts can be cleaved to the hydrazo-compounds by hydrazine hydrate. Cu(II) oxidation provides a route to azoalkanes: Synthesis, 543 (1981).

• Oxidation gives the aza-dienophile 4-phenyl-1,2,4-triazolinedione which is more reactive in cycloaddition reactions than tetracyanoethylene: J. Chem. Soc. (C), 1905 (1967); Angew. Chem. Int. Ed., 11, 715 (1972); Org. Prep. Proced. Int., 7, 251 (1975). Suitable oxidants include t-butyl hypochlorite: Org. Synth. Coll., 6, 936 (1988), or lead(IV) acetate: J. Org. Chem., 32, 330 (1967). For a further example, see Propargyltriphenylphosphonium bromide, A12753.

• Reacts with enolizable ketones in the presence of TFA to give ɑ-urazyl ketones: J. Org. Chem., 55, 193 (1990), which may be oxidized to ɑ-diketones with t-butyl hypochlorite: J. Org. Chem., 55, 197 (1990):