Picryl chloride

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.

Picryl chloride[1]
Names
IUPAC name
2-Chloro-1,3,5-trinitrobenzene
Other names
2,4,6-Trinitrochlorobenzene, 2-chloro-1,3,5-trinitrobenzene, TNCB
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.695
UNII
UN number 0155; 3365 (wetted)
Properties
C6H2ClN3O6
Molar mass 247.55 g/mol
Appearance Almost white or yellow needles
Melting point 83 °C
Hazards
R-phrases (outdated) R2 R26/27/28 R50/53
S-phrases (outdated) S28 S35 S36/37 S45 S60 S61
Explosive data
Detonation velocity 7,200 m/s
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

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:[2]

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.[3]

References

  1. 2-Chloro-1,3,5-trinitrobenzene at Sigma-Aldrich
  2. G. K. Helmkamp and D. J. Pettitt (1966). "Trimethyloxonium 2,4,6-Trinitrobenzenesulfonate". Org. Synth. 46: 122. doi:10.15227/orgsyn.046.0122.CS1 maint: uses authors parameter (link)
  3. Ross, S.; Bassin, M.; Finkelstein, M.; Leac, A. L. (1954). "Molecular Compounds. I. Picryl Chloride-Hexamethylbenzene in Chloroform Solution". J. Am. Chem. Soc. 76: 69–74. doi:10.1021/ja01630a018.CS1 maint: uses authors parameter (link)
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