Tetrachlorobenzene
{{Chembox
|ImageFile1 = 1,2,3,4-Tetrachlorobenzene.svg
|ImageSize1 = 82px
|ImageCaption1 = 1,2,3,4-Tetrachlorobenzene
|ImageFile2 = 1,2,3,5-Tetrachlorobenzene.svg
|ImageSize2 = 117px
|ImageCaption2 = 1,2,3,5-Tetrachlorobenzene
|ImageFile3 = 1,2,4,5-Tetrachlorobenzene.svg
|ImageSize3 = 117px
|ImageCaption3 = 1,2,4,5-Tetrachlorobenzene
|Section1={{Chembox Identifiers
| index_label = mix
| index5_label=1,2,3,4
| index4_label=1,2,3,5
| index3_label=1,2,4,5
| CASNo = 12408-10-5
| CASNo5 = 634-66-2
| CASNo4 = 634-90-2
| CASNo3 = 95-94-3
| ChEBI3 = 36697
| ChEBI4 = 36696
| ChEBI5 = 18855
| ChEMBL3 = 45428
| ChEMBL4 = 44011
| ChEMBL5 = 46422
| ChemSpiderID3 = 21106163
| ChemSpiderID4 = 21106571
| ChemSpiderID5 = 21106540
| DTXSID3 = DTXSID7024320
| DTXSID4 = DTXSID1026089
| DTXSID5 = DTXSID6026088
| EC_number3 = 202-466-2
| EC_number4 = 211-217-7
| EC_number5 = 211-214-0
| KEGG5 = C18236
| PubChem5 = 12463
| PubChem4 = 12468
| PubChem3 = 7270
| QID3 = Q2557079
| QID4 = Q27116931
| QID5 = Q27109095
| RTECS3 = DB9450000
| UNII3 = 5N27529KGH
| UNII4 = I27N186CIN
| UNII5 = MH0UY3V1KE
| InChI3=1S/C6H2Cl4/c7-3-1-4(8)6(10)2-5(3)9/h1-2H
| InChIKey3 = JHBKHLUZVFWLAG-UHFFFAOYSA-N
| SMILES3 = C1=C(C(=CC(=C1Cl)Cl)Cl)Cl
| InChI4=1S/C6H2Cl4/c7-3-1-4(8)6(10)5(9)2-3/h1-2H
| InChIKey4 = QZYNWJQFTJXIRN-UHFFFAOYSA-N
| SMILES4 = C1=C(C=C(C(=C1Cl)Cl)Cl)Cl
| InChI5=1S/C6H2Cl4/c7-3-1-2-4(8)6(10)5(3)9/h1-2H
| InChIKey5 = GBDZXPJXOMHESU-UHFFFAOYSA-N
| SMILES5 = C1=CC(=C(C(=C1Cl)Cl)Cl)Cl
}}
|Section2={{Chembox Properties
|C=6|H=2|Cl=4
}}
|Section8={{Chembox Related
}}
}}
Tetrachlorobenzene is any of three isomeric chlorobenzenes with the molecular formula {{chem2|C6H2Cl4}}. They differ by the positions of the chlorine atoms around the ring. Tetrachlorobenzenes are colorless crystalline compounds.{{cite book |doi=10.1002/14356007.o06_o03 |chapter=Chlorinated Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Beck |first1=Uwe |last2=Löser |first2=Eckhard |isbn=9783527303854 }}
Properties
| class="wikitable"
|+ Selected Physical Properties of Individual Isomers | |||
| isomer | m.p. (°C) | b.p. (°C) | m.p. (g/cm3 @100 °C) |
|---|---|---|---|
| 1,2,3,4 | 47 | 254 | 1.539 |
| 1,2,3,5 | 51.5 | 246 | 1.523 |
| 1,2,4,5 | 141 | 245 | 1.454 |
Synthesis
1,2,4,5-Tetrachlorobenzene can be produced by electrophilic halogenation of benzenes and some chlorobenzenes.{{cite web |title=US4205014A Process for 1,2,4,5-tetrachlorobenzene |url=https://worldwide.espacenet.com/patent/search/family/026711356/publication/US4205014A?q=pn%3DUS4205014A |publisher=Espacenet |access-date=22 June 2023}} 1,2,3,4-Tetrachlorobenzene can only be produced by chlorination of 1,3,5-trichlorobenzene.
Uses
1,2,4,5-Tetrachlorobenzene once was used as intermediates in the production of pesticides,{{cite book |title=NTP Toxicity Study Reports |date=1991 |publisher=National Toxicology Program |page=11 |url=https://books.google.com/books?id=4mrSWQi2luwC&dq=%2522Tetrachlorobenzene%2522&pg=PA11 |access-date=22 June 2023 |language=en}} specifically 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid.{{cite web |title=New Chlorobenzene Pesticides, Their Impacts on Environment and Food Quality |url=https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=272780c09baeee7985e9fab16809f267ce415801 |publisher=International Journal of Engineering Research and Science & Technology |date=November 2012}} This method has been discontinued because it also produced 2,3,7,8-tetrachlorodibenzo-p-dioxin.
See also
References
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