4-Phenylurazole

• Catalog No.: L00255
• CAS Number: 15988-11-1
• M. F.: C8H7N3O2
• M. W.: 177.16008
• Purity: 98+%

SYNONYMS

• Title: 4-苯基脲唑
• 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-Phenyl-1,2,4-triazolidine-3,5-dione

DATABASE IDS

• CAS Number: 15988-11-1
• EC Number: 240-127-0
• Beilstein Number: 163361
• MDL Number: MFCD00005226

PROPERTIES

• Purity: 98+%
• Melting Point: 206-210°C
• TSCA Listed: 是

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).