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

• ChemBase ID: 87227
• Molecular Formular: C8H7N3O2
• Molecular Mass: 177.16008
• Monoisotopic Mass: 177.05382648
• SMILES: n1(c2ccccc2)c(=O)[nH][nH]c1=O
• Canonical SMILES: O=c1[nH][nH]c(=O)n1c1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-phenyl-1,2,4-triazolidine-3,5-dione
• IUPAC Traditional name: 4-phenyl-1,2,4-triazolidine-3,5-dione
• Synonyms: 4-Phenylurazole 98%; 4-Phenyl-1,2,4-triazolidine-3,5-dione; 4-Phenylurazole; 4-Phenyl-1,2,4-triazolidine-3,5-dione; 4-苯基-1,2,4-三唑烷-3,5-二酮; 4-苯基脲唑

Database IDs

• CAS Number: 15988-11-1
• EC Number: 240-127-0
• MDL Number: MFCD00005226
• Beilstein Number: 163361
• PubChem SID: 162074343; 24851358
• PubChem CID: 85229

CALCULATED PROPERTIES

• Acid pKa: 12.884686
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.61370236
• LogD (pH = 7.4): 0.6137011
• Log P: 0.61370236
• Molar Refractivity: 44.4595 cm^3
• Polarizability: 16.87661 Å^3
• Polar Surface Area: 61.44 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 206-210°C; 207-209 °C(lit.)

Safety Information

• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%; 98+%
• Empirical Formula (Hill Notation): C8H7N3O2

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

REFERENCES

• 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):
  
• ?-Diketones form adducts without an added catalyst. These yield 1,2,3-triketones on cleavage.
• Review of use of azodicarbonyl compounds in synthesis: Adv. Het. Chem., 30, 1 (1982).
• 1,2,4-Triazolinediones form charge-transfer complexes with electron-rich aromatics, such as di- or trimethoxybenzenes: J. Org. Chem., 48, 1708 (1983).
• 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.
• The adducts can be cleaved to the hydrazo-compounds by hydrazine hydrate. Cu(II) oxidation provides a route to azoalkanes: Synthesis, 543 (1981).