1,2,4-Trimethylbenzene

changed 477184191 7929 1,2,4-Trimethylbenzene 1,2,4-Trimethylbenzene-2D-structure.svg Skeletal formula skin-invert 1,2,4-Trimethylbenzene-3D-balls.png Ball-and-stick model bg-transparent 1,2,4-Trimethylbenzene 1,2,4-Trimethylbenzene Pseudocumene Asymmetrical trimethylbenzene Ψ-Cumene correct CAS 95-63-6 1903005 correct EBI 34039 1797280 correct chemspider 6977 202-436-9 correct kegg C14533 7247 DC3325000 1993 2325 1/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3 GWHJZXXIDMPWGX-UHFFFAOYAF correct chemspider 1S/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3 correct chemspider GWHJZXXIDMPWGX-UHFFFAOYSA-N correct FDA 34X0W8052F c1c(ccc(c1C)C)C 3–534, 5–176, 6–82, 6–153, 6–163 9 12 0.8758 g/cm3 (20 C) Colorless liquid -43.8 169.4 649.1 K at 3.3 MPa 0.057 g/L 3.63 2.3 hPa (20 C) -101.6 -6 cm3/mol 1.5048 (20 C) 13.19 kJ.mol-1 47.93 kJ.mol-1 (25 C) t73601 1,2,4-Trimethylbenzene 02 08 07 09 Danger 226 304 315 319 332 335 411 210 233 240 241 242 243 261 264 271 273 280 301+310 303+361+353 304+340+312 305+351+338 331 332+313 337+313 362 370+378 391 403+233 403+235 405 501 2 2 0 - SDS - 1,2,4-trimethylbenzene https://documents.thermofisher.com/DirectWebViewer/private/document.aspx?prd=ALFAA12411~~PDF~~MTR~~AGHS~~EN~~2025-12-23%2018:28:31~~1%202%204-Trimethylbenzene~~ documents.thermofisher.com Revision #4 ThermoFisher Scientific 2 June 2026 3 pdf 22 December 2025 48 515 0.9 - 6.4 % 25 ppm 0638 1,2,3-Trimethylbenzene 1,3,5-Trimethylbenzene 1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, 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 coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene. History In 1849, Charles Blachford Mansfield rectified coal tar and identified fractions which he hypothesized to be cumole and cymole. The latter fraction boiled slightly above 170 C and had specific density of 0.857.Mansfield Charles Blachford 1849 Researches on coal tar https://books.google.com/books?id=QQjzAAAAMAAJ&pg=PA267 Quarterly Journal of the Chemical Society of London en 1 3 244-68 10.1039/QJ8490100244 1743-6893 In 1862, Warren De la Rue and Hugo Müller (1833-1915) proposed the term pseudocumole for the fractions heavier than xylole.DeLaRue Warren Müller Hugo 1862 On some products of the action of dilute nitric acid on some hydrocarbons of the benzol series. (Preliminary notice.) Quarterly Journal of the Chemical Society of London en 14 1 54-7 10.1039/QJ8621400054 1743-6893 When three years later American chemist Cyrus Warren (1824-1891) attempted to reproduce Mansfield's results, he determined that the oil boiling at 170 C has the same formula as cumole, not cymole, and suggested to name it isocumole.https://books.google.com/books?id=xWkWAAAAYAAJ&pg=RA1-PA106 The American Journal of Science and Arts 1865 S. Converse en The structure of the compound was determined by Th. Ernst and Wilhelm Rudolph Fittig, who first prepared it from bromoxylene and iodomethane in 1866 by a Wurtz–Fittig reaction developed two years earlier.Ernst Th. Fittig Rud. 1866 Ueber das Methyl‐ und Aethylxylol Justus Liebigs Annalen der Chemie en 139 2 184-98 10.1002/jlac.18661390208 0075-4617 In the next year, Fittig et al. adopted the pseudocumol terminology,Fitig Rud. Köbrich A. Jilke T. 1868 Ueber die Zersetzung des Camphers durch schmelzendes Chlorzink https://books.google.com/books?id=HupSAAAAcAAJ&pg=PA138 Justus Liebigs Annalen der Chemie en 145 2 129-57 10.1002/jlac.18681450202 0075-4617 in 1869 Fittig and B. Wackenroder proved that the fraction is a mixture of mesitylene with another trimethylbenzene, for which the name of pseudocumol was retained,Fittig Rud. Wackenroder B. 1869 Ueber das im Steinkohlentheer enthaltene Trimethylbenzol https://books.google.com/books?id=FLI9AQAAMAAJ&pg=PA297 Justus Liebigs Annalen der Chemie en 151 3 292–298 10.1002/jlac.18691510304 0075-4617 and in 1886 Oscar Georg Friedrich Jacobsen Oscar Jacobsen de Oscar Jacobsen showed that the third trimethylbenzene he discovered earlier is also present.Jacobsen Oscar 1886 Beitrag zur Kenntniss der zwischen 170 und 200° siedenden Kohlenwasserstoffe des Steinkohlentheeröls https://books.google.com/books?id=YzBJAAAAYAAJ&pg=PA2511 Berichte der deutschen chemischen Gesellschaft en 19 2 2511-5 10.1002/cber.188601902195 0365-9496 Production Industrially, it is isolated from the C9 aromatic hydrocarbon fraction during petroleum distillation. Approximately 40% of this fraction is 1,2,4-trimethylbenzene. It is also generated by methylation of toluene and xylenes and the disproportionation of xylene over aluminosilicate catalysts.Karl Griesbaum Arno Behr Dieter Biedenkapp Heinz-Werner Voges Dorothea Garbe Christian Paetz Gerd Collin Dieter Mayer Hartmut Höke Hydrocarbons 2002 10.1002/14356007.a13_227 Uses Pseudocumene is a precursor to trimellitic anhydride, 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 an antiknock agent,2008-01-28 text United States Environmental Protection Agency 1994-08-01 http://www.epa.gov/chemfact/s_trimet.txt Chemical Summary for 1,2,4-Trimethylbenzene https://web.archive.org/web/20080618213236/http://www.epa.gov/chemfact/s_trimet.txt 18 June 2008 since its research and motor octane numbers are well above 100.Scherzer Julius https://books.google.com/books?id=0R2qSCsVT3cC&pg=PA10 Octane-Enhancing Zeolitic FCC Catalysts: Scientific and Technical Aspects 1990 CRC Press 978-0-8247-8399-0 10 enFig. II.1Simanzhenkov V. Idem R. Crude Oil Chemistry CRC Press 2003 978-0-203-01404-2 https://books.google.com/books?id=om8pgoU-KiMC&pg=PA41 27 December 2024 41 In automobile fuel it is a minor additive, with its share in US gasoline rising from 0.03 - 0.5 % in early 1990sDoskey Paul V. Porter Joseph A. Scheff Peter A. November 1992 Source Fingerprints for Volatile Non-Methane Hydrocarbons Journal of the Air & Waste Management Association en 42 11 1437-45 10.1080/10473289.1992.10467090 1047-3289 to 1.1 - 2.6 % in 2011.2011 Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100GPED.TXT nepis.epa.gov United States Environmental Protection Agency It may be a major component of some avgas formulations.9593285B2 Scintillator 1,2,4-Trimethylbenzene dissolved in mineral oil is used as a liquid scintillatoretal Liquid scintillator production for the NOvA experiment Nuclear Instruments and Methods A 799 1–9 November 1, 2015 Mufson S. 10.1016/j.nima.2015.07.026 1504.04035 2015NIMPA.799....1M 118578183 in particle physics experiments such as NOνA and Borexino. See also Cumene References Category:Alkylbenzenes Category:C3-Benzenes