Picryl chloride
![]() | |
Names | |
---|---|
Preferred IUPAC name 2-Chloro-1,3,5-trinitrobenzene | |
Other names 2,4,6-Trinitrochlorobenzene, 2-chloro-1,3,5-trinitrobenzene, TNCB | |
Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
ChemSpider |
|
ECHA InfoCard | 100.001.695 ![]() |
EC Number |
|
PubChem CID |
|
UNII |
|
UN number | 0155; 3365 (wetted) |
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | C6H2ClN3O6 |
Molar mass | 247.55 g/mol |
Appearance | Almost white or yellow needles |
Melting point | 83 °C |
Hazards | |
GHS labelling: | |
Pictograms | ![]() ![]() ![]() |
Danger | |
Hazard statements | H201, H300, H310, H330, H410 |
Precautionary statements | 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). ![]() ![]() ![]() Infobox references |
Chemical compound
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
- ^ 2-Chloro-1,3,5-trinitrobenzene at Sigma-Aldrich
- ^ G. K. Helmkamp; D. J. Pettitt (1966). "Trimethyloxonium 2,4,6-Trinitrobenzenesulfonate". Org. Synth. 46: 122. doi:10.15227/orgsyn.046.0122.
- ^ 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.
- v
- t
- e