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1,2,4-Trimethylbenzene

Names
Preferred IUPAC name 1,2,4-Trimethylbenzene
Other names Pseudocumene, Asymmetrical trimethylbenzene, ψ-Cumene
Identifiers
CAS Number	95-63-6
3D model (JSmol)	Interactive image
Beilstein Reference	1903005
ChEBI	CHEBI:34039
ChEMBL	ChEMBL1797280
ChemSpider	6977
ECHA InfoCard	100.002.216
EC Number	202-436-9
KEGG	C14533
PubChem CID	7247
RTECS number	DC3325000
UNII	34X0W8052F
UN number	1993 2325
CompTox Dashboard (EPA)	DTXSID6021402
InChI InChI=1S/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3Key: GWHJZXXIDMPWGX-UHFFFAOYSA-N InChI=1/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3Key: GWHJZXXIDMPWGX-UHFFFAOYAF
SMILES c1c(ccc(c1C)C)C
Properties
Chemical formula	C9H12
Molar mass	120.19 g/mol
Appearance	Colorless liquid
Density	0.8761 g/cm
Melting point	−43.78 °C (−46.80 °F; 229.37 K)
Boiling point	169 to 171 °C (336 to 340 °F; 442 to 444 K)
Magnetic susceptibility (χ)	-101.6·10 cm/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319, H332, H335, H411
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point	44.4 °C (111.9 °F; 317.5 K)
Explosive limits	0.9%–6.4%
NIOSH (US health exposure limits):
PEL (Permissible)	none
Safety data sheet (SDS)	Sigma-Aldrich MSDS
Related compounds
Related compounds	1,2,3-Trimethylbenzene; 1,3,5-Trimethylbenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

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.

In 1862, Warren De la Rue and Hugo Müller (1833-1915) proposed the term pseudocumole for the fractions heavier than xylole.

When three years later American chemist Cyrus Warren (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.

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.

In the next year, Fittig et al. adopted the pseudocumol terminology, 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, and in 1886 Oscar Jacobsen [de] showed that the third trimethylbenzene he discovered earlier is also present.

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.

Uses

Pseudocumene is a precursor to mellitic 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 a gasoline additive.

Scintillator

1,2,4-Trimethylbenzene dissolved in mineral oil is used as a liquid scintillator in particle physics experiments such as NOνA and Borexino.

See also

• Cumene

References

1. Merck Index, 11th Edition, 7929
2. ^ NIOSH Pocket Guide to Chemical Hazards. "#0638". National Institute for Occupational Safety and Health (NIOSH).
3. Mansfield, Charles Blachford (1849). "Researches on coal tar". Quarterly Journal of the Chemical Society of London. 1 (3): 244–268. doi:10.1039/QJ8490100244. ISSN 1743-6893.
4. 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. 14 (1): 54–57. doi:10.1039/QJ8621400054. ISSN 1743-6893.
5. The American Journal of Science and Arts. S. Converse. 1865.
6. Ernst, Th.; Fittig, Rud. (1866). "Ueber das Methyl‐ und Aethylxylol". Justus Liebigs Annalen der Chemie. 139 (2): 184–198. doi:10.1002/jlac.18661390208. ISSN 0075-4617.
7. Fitig, Rud.; Köbrich, A.; Jilke, T. (1868). "Ueber die Zersetzung des Camphers durch schmelzendes Chlorzink". Justus Liebigs Annalen der Chemie. 145 (2): 129–157. doi:10.1002/jlac.18681450202. ISSN 0075-4617.
8. Fittig, Rud.; Wackenroder, B. (1869). "Ueber das im Steinkohlentheer enthaltene Trimethylbenzol". Justus Liebigs Annalen der Chemie. 151 (3): 292–298. doi:10.1002/jlac.18691510304. ISSN 0075-4617.
9. Jacobsen, Oscar (1886). "Beitrag zur Kenntniss der zwischen 170 und 200° siedenden Kohlenwasserstoffe des Steinkohlentheeröls". Berichte der deutschen chemischen Gesellschaft. 19 (2): 2511–2515. doi:10.1002/cber.188601902195. ISSN 0365-9496.
10. 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
11. "Chemical Summary for 1,2,4-Trimethylbenzene" (text). United States Environmental Protection Agency. 1994-08-01. Retrieved 2008-01-28.
12. Mufson, S.; et al. (November 1, 2015). "Liquid scintillator production for the NOvA experiment". Nuclear Instruments and Methods A. 799: 1–9. arXiv:1504.04035. Bibcode:2015NIMPA.799....1M. doi:10.1016/j.nima.2015.07.026. S2CID 118578183.

External links

• EPA Chemical Fact Sheet
• CDC – NIOSH Pocket Guide to Chemical Hazards

• Alkylbenzenes
• C3-Benzenes