| Revision as of 19:04, 9 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 22:06, 3 February 2024 edit undoMichael7604 (talk | contribs)Extended confirmed users8,895 edits recategorized from Nitrobenzenes to Nitrobenzene derivatives |
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| verifiedrevid = 416997580 |
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|Reference=<ref> at ]</ref> |
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| verifiedrevid = 418001633 |
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|ImageFile=Picryl chloride.png |
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| Reference=<ref> at ]</ref> |
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|ImageSize=150px |
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| ImageFile=2,4,6-Trinitrochlorobenzene.png |
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|IUPACName=2-Chloro-1,3,5-trinitrobenzene |
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| ImageSize=150px |
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|OtherNames=2,4,6-Trinitrochlorobenzene |
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| PIN=2-Chloro-1,3,5-trinitrobenzene |
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| OtherNames=2,4,6-Trinitrochlorobenzene, 2-chloro-1,3,5-trinitrobenzene, TNCB |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=88-88-0 |
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| CASNo=88-88-0 |
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| EINECS = 201-864-3 |
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| PubChem=6953 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNNumber = 0155; 3365 (wetted) |
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| UNII = Z4ZG7O5SZ9 |
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| SMILES=C1=C(C=C(C(=C1(=O))Cl)(=O))(=O) |
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| PubChem=6953 |
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| UNNumber = 0155; 3365 (wetted) |
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| SMILES=C1=C(C=C(C(=C1(=O))Cl)(=O))(=O) |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 6687 |
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| InChI = 1/C6H2ClN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H |
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| InChIKey = HJRJRUMKQCMYDL-UHFFFAOYAU |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C6H2ClN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = HJRJRUMKQCMYDL-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>6</sub>H<sub>2</sub>ClN<sub>3</sub>O<sub>6</sub> |
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| Formula=C<sub>6</sub>H<sub>2</sub>ClN<sub>3</sub>O<sub>6</sub> |
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| MolarMass=247.55 g/mol |
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| MolarMass=247.55 g/mol |
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| Appearance= |
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| Appearance=Almost white or yellow needles |
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| MeltingPt=83 °C |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| RPhrases = {{R2}} {{R26/27/28}} {{R50/53}} |
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| GHSPictograms = {{GHS01}}{{GHS06}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| SPhrases = {{S28}} {{S35}} {{S36/37}} {{S45}} {{S60}} {{S61}} |
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| HPhrases = {{H-phrases|201|300|310|330|410}} |
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| 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}} |
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| Section6 = {{Chembox Explosive |
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|Section6={{Chembox Explosive |
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| ExplosiveV = 7,200 m/s |
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| DetonationV = 7,200 m/s |
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'''Picryl chloride''' is an ] also known as '''2-chloro-1,3,5-trinitrobenzene''' or '''2,4,6-trinitrochlorobenzene''' (TNCB). Its empirical formula is C<sub>6</sub>H<sub>2</sub>ClN<sub>3</sub>O<sub>6</sub>. Its ] is 7,200 m/s. |
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'''Picryl chloride''' is an ] with the formula ClC<sub>6</sub>H<sub>2</sub>(NO<sub>2</sub>)<sub>3</sub>. It is a bright yellow solid that is highly explosive, as is typical for polynitro aromatics such as ]. Its ] is 7,200 m/s. |
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==Reactions== |
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The reactivity of picryl chloride is strongly influenced by the presence of three ] ]s. Consequently picryl chloride is an electrophile as illustrated by its reactivity toward ] to give the ]:<ref>{{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 |
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|doi=10.15227/orgsyn.046.0122}}</ref> |
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:ClC<sub>6</sub>H<sub>2</sub>(NO<sub>2</sub>)<sub>3</sub> + Na<sub>2</sub>SO<sub>3</sub> → NaO<sub>3</sub>SC<sub>6</sub>H<sub>2</sub>(NO<sub>2</sub>)<sub>3</sub> + NaCl |
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Picryl chloride is also a strong electron acceptor. It forms a 1:1 ] with ].<ref>{{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}}</ref> |
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==References== |
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==References== |
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