Picryl chloride
Names | |
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IUPAC name
2-Chloro-1,3,5-trinitrobenzene
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Other names
2,4,6-Trinitrochlorobenzene, 2-chloro-1,3,5-trinitrobenzene, TNCB
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.001.695 |
PubChem CID
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UNII | |
UN number | 0155; 3365 (wetted) |
CompTox Dashboard (EPA)
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Properties | |
C6H2ClN3O6 | |
Molar mass | 247.55 g/mol |
Appearance | Almost white or yellow needles |
Melting point | 83 °C |
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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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
- ^ "Trimethyloxonium 2,4,6-Trinitrobenzenesulfonate". Org. Synth. 46: 122. 1966. doi:10.15227/orgsyn.046.0122.
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(help) - ^ "Molecular Compounds. I. Picryl Chloride-Hexamethylbenzene in Chloroform Solution". J. Am. Chem. Soc. 76: 69–74. 1954. doi:10.1021/ja01630a018.
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