Picryl chloride
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 418001633
| Reference=[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=79874|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 2-Chloro-1,3,5-trinitrobenzene] at Sigma-Aldrich
| ImageFile=2,4,6-Trinitrochlorobenzene.png
| ImageSize=150px
| PIN=2-Chloro-1,3,5-trinitrobenzene
| OtherNames=2,4,6-Trinitrochlorobenzene, 2-chloro-1,3,5-trinitrobenzene, TNCB
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=88-88-0
| EINECS = 201-864-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z4ZG7O5SZ9
| PubChem=6953
| UNNumber = 0155; 3365 (wetted)
| SMILES=C1=C(C=C(C(=C1[N+](=O)[O-])Cl)[N+](=O)[O-])[N+](=O)[O-]
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 6687
| InChI = 1/C6H2ClN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H
| InChIKey = HJRJRUMKQCMYDL-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H2ClN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = HJRJRUMKQCMYDL-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula=C6H2ClN3O6
| MolarMass=247.55 g/mol
| Appearance=Almost white or yellow needles
| Density=
| MeltingPt=83 °C
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
| GHSPictograms = {{GHS01}}{{GHS06}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|201|300|310|330|410}}
| PPhrases = {{P-phrases|210|230|240|250|260|262|264|270|271|273|280|284|301+310|302+350|304+340|310|320|321|322|330|361|363|370+380|372|373|391|401|403+233|405|501}}
}}
|Section6={{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV = 7,200 m/s
| REFactor =
}}
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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:{{cite journal|title=Trimethyloxonium 2,4,6-Trinitrobenzenesulfonate|author1=G. K. Helmkamp |author2=D. J. Pettitt |journal=Org. Synth.|year=1966|volume=46|pages=122
|doi=10.15227/orgsyn.046.0122}}
: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.{{cite journal|author1=Ross, S. |author2=Bassin, M. |author3=Finkelstein, M. |author4=Leac, A. L. |title=Molecular Compounds. I. Picryl Chloride-Hexamethylbenzene in Chloroform Solution|journal=J. Am. Chem. Soc.|year=1954|volume=76|pages=69–74|doi=10.1021/ja01630a018}}