4-Dimethylaminophenylpentazole

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4-Dimethylaminophenylpentazole
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4-Dimethylaminophenylpentazole molecule
Names
IUPAC name
4-dimethylaminophenylpentazole
Identifiers
ChemSpider 10447638 YesY
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PubChem 23279314
  • InChI=1S/C8H10N6/c1-13(2)7-3-5-8(6-4-7)14-11-9-10-12-14/h3-6H,1-2H3 YesY
    Key: OICBARXSRMXZPL-UHFFFAOYSA-N YesY
  • n1nnnn1-c2ccc(N(C)C)cc2
  • CN(C)c1ccc(cc1)n2nnnn2
Properties
C8H10N6
Molar mass 190.205
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Dimethylaminophenylpentazole is an unstable, explosive compound that contains the rare pentazole ring, which is composed of five nitrogen atoms. The electron donating effect of the 4-dimethylamino substituent on the phenyl ring makes this compound one of the more stable of the phenylpentazoles. At room temperature, its chemical half-life is only a few hours, although storage is possible at cryogenic temperatures. The compound was first prepared in 1956[1][2][3] along with other substituted phenylpentazoles. Studies have been conducted on various other derivatives, though necessarily limited by the instability of these compounds.[4][5][6][7][8] Some more highly substituted derivatives, such as 2,6-dihydroxy-4-dimethylaminophenylpentazole, are slightly more stable but conversely, more difficult to make.[9][10] Current research has focused on forming transition metal complexes of these pentazole derivatives, as the pentazole ring should be stabilised by bonding to the metal centre.[11][12][13]

References

  1. Huisgen R, I. Ugi. Zur Losung eines klassichen Problems der organischen Stickstoff-Chemie. Angewandte Chemie. 1956; 68:705-706.
  2. Ugi I, R. Huisgen. Pentazole II. Die Zerfallsgeschwindigkeit der Arylpentazole. Chemische Berichte. 1958; 91:531-537.
  3. Ugi I, Perlinger H, Perlinger L. Pentazole III. Kristallisierte Aryl-pentazole. Chemische Berichte 1958; 98:2324-2329,
  4. John D. Wallis and Jack D. Dunitz. An all-nitrogen aromatic ring system: structural study of 4-dimethyl-aminophenylpentazole. Journal of the Chemical Society. Chemical Communications. 1983: 910-911.
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  9. Efforts to synthesize the pentazolate anion
  10. David Adam. The synthesis and characterisation of halogen and nitro phenyl azide derivatives as highly energetic materials. PhD dissertation, Ludwig-Maximilans-Universität München, 2001 [1]
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