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Picryl chloride

Picryl chloride is an organic compound with the formula ClC<sub>6</sub>H<sub>2</sub>(NO<sub>2</sub>)<sub>3</sub>. 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:

ClC<sub>6</sub>H<sub>2</sub>(NO<sub>2</sub>)<sub>3</sub> + Na<sub>2</sub>SO<sub>3</sub> → NaO<sub>3</sub>SC<sub>6</sub>H<sub>2</sub>(NO<sub>2</sub>)<sub>3</sub> + NaCl

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

References