Picryl chloride

Source: Wikipedia, the free encyclopedia.
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

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. doi:10.15227/orgsyn.046.0122
    .
  3. doi:10.1021/ja01630a018
    .
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