Picryl chloride

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
CAS Number	88-88-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	6687 ;
ECHA InfoCard	100.001.695
PubChem CID	6953;
UNII	Z4ZG7O5SZ9 ;
UN number	0155; 3365 (wetted)
CompTox Dashboard (EPA)	DTXSID3025910 ;
	InChI InChI=1S/C6H2ClN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H Key: HJRJRUMKQCMYDL-UHFFFAOYSA-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;
	SMILES C1=C(C=C(C(=C1[N+](=O)[O-])Cl)[N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	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R-phrases (outdated)	R2 R26/27/28 R50/53
S-phrases (outdated)	S28 S35 S36/37 S45 S60 S61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

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 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)
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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[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)