Picryl chloride

Picryl chloride[1]
Names
Preferred 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 Edit this at Wikidata
EC Number
  • 201-864-3
UNII
UN number 0155; 3365 (wetted)
  • InChI=1S/C6H2ClN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H ☒N
    Key: HJRJRUMKQCMYDL-UHFFFAOYSA-N ☒N
  • InChI=1/C6H2ClN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H
    Key: HJRJRUMKQCMYDL-UHFFFAOYAU
  • C1=C(C=C(C(=C1[N+](=O)[O-])Cl)[N+](=O)[O-])[N+](=O)[O-]
Properties
C6H2ClN3O6
Molar mass 247.55 g/mol
Appearance Almost white or yellow needles
Melting point 83 °C
Hazards
GHS labelling:
GHS01: ExplosiveGHS06: ToxicGHS09: Environmental hazard
Danger
H201, H300, H310, H330, H410
P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P370+P380, P372, P373, P391, P401, P403+P233, P405, P501
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).
☒N verify (what is checkY☒N ?)

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:[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; D. J. Pettitt (1966). "Trimethyloxonium 2,4,6-Trinitrobenzenesulfonate". Org. Synth. 46: 122. doi:10.15227/orgsyn.046.0122.
  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.
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