| Revision as of 13:59, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 461589366 of page 1,2,4-Trimethylbenzene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 11:30, 18 November 2024 edit 5.178.188.143 (talk) →HistoryTag: Visual edit |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{chembox |
|
|
|Watchedfields = changed |
|
| verifiedrevid = 444391152 |
|
|
|
|verifiedrevid = 477184191 |
|
| Reference=<ref>'']'', 11th Edition, '''7929'''</ref> |
|
|
|
|Reference =<ref>'']'', 11th Edition, '''7929'''</ref> |
|
| Name = 1,2,4-Trimethylbenzene |
|
|
| ImageFileL1 = 1,2,4-Trimethylbenzene.svg |
|
|Name = 1,2,4-Trimethylbenzene |
|
|
|ImageFileL1 = 1,2,4-Trimethylbenzene-2D-structure.svg |
|
| ImageSizeL1 = 105px |
|
|
| ImageNameL1 = Skeletal formula |
|
|ImageNameL1 = Skeletal formula |
|
| ImageFileR1 = 1,2,4-Trimethylbenzene-3D-balls.png |
|
|ImageFileR1 = 1,2,4-Trimethylbenzene-3D-balls.png |
|
|
|ImageNameR1 = Ball-and-stick model |
|
| ImageSizeR1 = 115px |
|
|
|
|ImageName = 1,2,4-Trimethylbenzene |
|
| ImageNameR1 = Ball-and-stick model |
|
|
| ImageName = 1,2,4-Trimethylbenzene |
|
|PIN = 1,2,4-Trimethylbenzene |
|
|
|OtherNames = Pseudocumene,<br />Asymmetrical trimethylbenzene,<br />ψ-Cumene |
|
| IUPACName = 1,2,4-Trimethylbenzene |
|
|
|
|Section1={{Chembox Identifiers |
|
| OtherNames = Pseudocumene,<br />Asymmetrical trimethylbenzene,<br />psi-cumene |
|
|
|
|CASNo_Ref = {{cascite|correct|CAS}} |
|
| Section1 = {{Chembox Identifiers |
|
|
|
|CASNo = 95-63-6 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
|Beilstein = 1903005 |
|
|
|ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI = 34039 |
|
|ChEBI = 34039 |
|
|
|ChEMBL = 1797280 |
|
| ChemSpiderID = 6977 |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|ChemSpiderID = 6977 |
|
| KEGG = C14533 |
|
|
|
|EC_number = 202-436-9 |
|
| InChI = 1/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3 |
|
|
|
|KEGG_Ref = {{keggcite|correct|kegg}} |
|
| InChIKey = GWHJZXXIDMPWGX-UHFFFAOYAF |
|
|
|
|KEGG = C14533 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|PubChem = 7247 |
|
| StdInChI = 1S/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3 |
|
|
|
|RTECS = DC3325000 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|UNNumber = 1993 2325 |
|
| StdInChIKey = GWHJZXXIDMPWGX-UHFFFAOYSA-N |
|
|
|
|InChI = 1/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3 |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
|
|InChIKey = GWHJZXXIDMPWGX-UHFFFAOYAF |
|
| CASNo = 95-63-6 |
|
|
|
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| SMILES = c1c(ccc(c1C)C)C |
|
|
|
|StdInChI = 1S/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3 |
|
|
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|StdInChIKey = GWHJZXXIDMPWGX-UHFFFAOYSA-N |
|
|
|UNII_Ref = {{fdacite|correct|FDA}} |
|
|
|UNII = 34X0W8052F |
|
|
|SMILES = c1c(ccc(c1C)C)C |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula = C<sub>9</sub>H<sub>12</sub> |
|
|Formula = C{{sub|9}}H{{sub|12}} |
|
| MolarMass = 120.19 g/mol |
|
|MolarMass = 120.19 g/mol |
|
| Density = 0.8761 g/cm³ |
|
|Density = 0.8761 g/cm{{sup|3}} |
|
|
|Appearance = Colorless liquid |
|
| MeltingPt = -43.78 °C |
|
|
|
|MeltingPtC = -43.78 |
|
| BoilingPt = 169-171 °C |
|
|
|
|BoilingPtC = 169 to 171 |
|
}} |
|
|
|
|MagSus = -101.6·10{{sup|−6}} cm{{sup|3}}/mol |
|
| Section3 = {{Chembox Hazards |
|
|
| EUClass = Harmful (Xn); Dangerous for the environment (N) |
|
|
| ExternalMSDS = }} |
|
|
}} |
|
}} |
|
|
|Section3={{Chembox Hazards |
|
|
|FlashPtC = 44.4 |
|
|
|ExternalSDS = |
|
|
|PEL = none<ref name=PGCH>{{PGCH|0638}}</ref> |
|
|
|ExploLimits = 0.9%–6.4%<ref name=PGCH/> |
|
|
|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS09}} |
|
|
|GHSSignalWord = Warning |
|
|
|HPhrases = {{H-phrases|226|315|319|332|335|411}} |
|
|
|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|302+352|303+361+353|304+312|304+340|305+351+338|312|321|332+313|337+313|362|370+378|391|403+233|403+235|405|501}} |
|
|
}} |
|
|
|Section4={{Chembox Related |
|
|
|OtherCompounds = ]; ] |
|
|
}} |
|
|
}} |
|
|
'''1,2,4-Trimethylbenzene''', also known as '''pseudocumene''', is an ] with the chemical formula C{{sub|6}}H{{sub|3}}(CH{{sub|3}}){{sub|3}}. Classified as an ], it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in ] and ] (about 3%). It is one of the three ] of ]. |
|
|
|
|
|
==History== |
|
|
In 1849, ] rectified ] and identified fractions which he hypothesized to be ] and ]. The latter fraction boiled slightly above 170°C and had specific density of 0.857.<ref>{{Cite journal |last=Mansfield |first=Charles Blachford |date=1849 |title=Researches on coal tar |url=https://books.google.com/books?id=QQjzAAAAMAAJ&pg=PA267 |journal=Quarterly Journal of the Chemical Society of London |language=en |volume=1 |issue=3 |pages=244–268 |doi=10.1039/QJ8490100244 |issn=1743-6893}}</ref> |
|
|
|
|
|
In 1862, ] and Hugo Müller (1833-1915) proposed the term '''pseudocumole''' for the fractions heavier than ].<ref>{{Cite journal |last=DeLaRue |first=Warren |last2=Müller |first2=Hugo |date=1862 |title=On some products of the action of dilute nitric acid on some hydrocarbons of the benzol series. (Preliminary notice.) |url=https://pubs.rsc.org/en/content/articlelanding/1862/qj/qj8621400054 |journal=Quarterly Journal of the Chemical Society of London |language=en |volume=14 |issue=1 |pages=54–57 |doi=10.1039/QJ8621400054 |issn=1743-6893}}</ref> |
|
|
|
|
|
When three years later American chemist ] (1824-1891) attempted to reproduce Mansfield's results, he determined that the oil boiling at 170° has the same formula as cumole, not cymole, and suggested to name it '''isocumole'''.<ref>{{Cite book |url=https://books.google.com/books?id=xWkWAAAAYAAJ&pg=RA1-PA106 |title=The American Journal of Science and Arts |date=1865 |publisher=S. Converse |language=en}}</ref> |
|
|
|
|
|
The structure of the compound was determined by Th. Ernst and ], who first prepared it from ] and ] in 1866 by a ] developed two years earlier.<ref>{{Cite journal |last=Ernst |first=Th. |last2=Fittig |first2=Rud. |date=1866 |title=Ueber das Methyl‐ und Aethylxylol |url=https://books.google.com/books?id=0bA9AQAAMAAJ&pg=PA184 |journal=Justus Liebigs Annalen der Chemie |language=en |volume=139 |issue=2 |pages=184–198 |doi=10.1002/jlac.18661390208 |issn=0075-4617}}</ref> |
|
|
|
|
|
In the next year, Fittig et al. adopted the pseudocumol terminology,<ref>{{Cite journal |last=Fitig |first=Rud. |last2=Köbrich |first2=A. |last3=Jilke |first3=T. |date=1868 |title=Ueber die Zersetzung des Camphers durch schmelzendes Chlorzink |url=https://books.google.com/books?id=HupSAAAAcAAJ&pg=PA138 |journal=Justus Liebigs Annalen der Chemie |language=en |volume=145 |issue=2 |pages=129–157 |doi=10.1002/jlac.18681450202 |issn=0075-4617}}</ref> in 1869 Fittig and B. Wackenroder proved that the fraction is a mixture of ] with another trimethylbenzene, for which the name of pseudocumol was retained,<ref>{{Cite journal |last=Fittig |first=Rud. |last2=Wackenroder |first2=B. |date=1869 |title=Ueber das im Steinkohlentheer enthaltene Trimethylbenzol |url=https://books.google.com/books?id=FLI9AQAAMAAJ&pg=PA297 |journal=Justus Liebigs Annalen der Chemie |language=en |volume=151 |issue=3 |pages=292–298 |doi=10.1002/jlac.18691510304 |issn=0075-4617}}</ref> and in 1886 {{Ill|Oscar Georg Friedrich Jacobsen|lt=Oscar Jacobsen|de|Oscar Jacobsen}} showed that the ] he discovered earlier is also present.<ref>{{Cite journal |last=Jacobsen |first=Oscar |date=1886 |title=Beitrag zur Kenntniss der zwischen 170 und 200° siedenden Kohlenwasserstoffe des Steinkohlentheeröls |url=https://books.google.com/books?id=YzBJAAAAYAAJ&pg=PA2511 |journal=Berichte der deutschen chemischen Gesellschaft |language=en |volume=19 |issue=2 |pages=2511–2515 |doi=10.1002/cber.188601902195 |issn=0365-9496}}</ref> |
|
|
|
|
|
== Production == |
|
|
Industrially, it is isolated from the C{{sub|9}} ] fraction during ]. Approximately 40% of this fraction is 1,2,4-trimethylbenzene. It is also generated by methylation of toluene and xylenes and the ] of xylene over aluminosilicate catalysts.<ref name=Ullmanns>Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke "Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a13_227}}</ref> |
|
|
|
|
|
==Uses== |
|
|
Pseudocumene is a precursor to ], from which high performance polymers are made. It is also used as a sterilizing agent and in the making of dyes, perfumes and resins. Another use is as a ].<ref>{{cite web|accessdate =2008-01-28| format =text| publisher=]| date =1994-08-01| url =http://www.epa.gov/chemfact/s_trimet.txt| title =Chemical Summary for 1,2,4-Trimethylbenzene}}</ref> |
|
|
|
|
|
===Scintillator=== |
|
|
1,2,4-Trimethylbenzene dissolved in ] is used as a liquid ]<ref name="NIMA.799.1">{{cite journal |display-authors=etal| title=Liquid scintillator production for the NOvA experiment |journal=Nuclear Instruments and Methods A | volume=799 | pages=1–9|date=November 1, 2015 |last=Mufson |first=S.|doi=10.1016/j.nima.2015.07.026|arxiv=1504.04035| bibcode=2015NIMPA.799....1M| s2cid=118578183 }}</ref> in particle physics experiments such as ] and ]. |
|
|
|
|
|
==See also== |
|
|
* ] |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
|
|
|
|
==External links== |
|
|
* |
|
|
* |
|
|
|
|
|
{{Hydrocarbons}} |
|
|
|
|
|
{{DEFAULTSORT:Trimethylbenzene, 1, 2, 4-}} |
|
|
] |
|
|
] |