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15988-11-1 - 4-Phenylurazole, 98+% - 4-Phenyl-1,2,4-triazolidine-3,5-dione - L00255 - Alfa Aesar

L00255 4-Phenylurazole, 98+%

CAS Number
15988-11-1
Synonyms
4-Phenyl-1,2,4-triazolidine-3,5-dione

Size Price ($) Quantity Availability
5g 21.91
25g 73.26
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4-Phenylurazole, 98+%

MDL
MFCD00005226
EINECS
240-127-0

Chemical Properties

Formula
C8H7N3O2
Formula Weight
177.16
Melting point
206-210°

Literature References

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.

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

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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):

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

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Review of use of azodicarbonyl compounds in synthesis: Adv. Het. Chem., 30, 1 (1982).

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

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Other References

Beilstein
163361
Harmonized Tariff Code
2933.99
TSCA
Yes

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