Picryl chloride explained

Picryl chloride is an organic compound with the formula ClC6H2(NO2)3. It is a bright yellow solid that is highly explosive, as is typical for polynitro aromatics such as picric acid. Its detonation velocity is 7,200 m/s.

Reactions

The reactivity of picryl chloride is strongly influenced by the presence of three electron-withdrawing nitro groups. Consequently picryl chloride is an electrophile as illustrated by its reactivity toward sulfite to give the sulfonate:[1]

ClC6H2(NO2)3 + Na2SO3 → NaO3SC6H2(NO2)3 + NaCl

Picryl chloride is also a strong electron acceptor. It forms a 1:1 charge-transfer complex with hexamethylbenzene.[2]

Notes and References

  1. Trimethyloxonium 2,4,6-Trinitrobenzenesulfonate. G. K. Helmkamp . D. J. Pettitt . Org. Synth.. 1966. 46. 122. 10.15227/orgsyn.046.0122.
  2. Ross, S. . Bassin, M. . Finkelstein, M. . Leac, A. L. . Molecular Compounds. I. Picryl Chloride-Hexamethylbenzene in Chloroform Solution. J. Am. Chem. Soc.. 1954. 76. 69–74. 10.1021/ja01630a018.

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