1,2,4-Trimethylbenzene

Last updated
1,2,4-Trimethylbenzene [1]
Skeletal formula 1,2,4-Trimethylbenzene-2D-structure.svg
Skeletal formula
Ball-and-stick model 1,2,4-Trimethylbenzene-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
1,2,4-Trimethylbenzene
Other names
Pseudocumene,
Asymmetrical trimethylbenzene,
ψ-Cumene
Identifiers
3D model (JSmol)
1903005
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.216 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-436-9
KEGG
PubChem CID
RTECS number
  • DC3325000
UNII
UN number 1993 2325
  • InChI=1S/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3 Yes check.svgY
    Key: GWHJZXXIDMPWGX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3
    Key: GWHJZXXIDMPWGX-UHFFFAOYAF
  • c1c(ccc(c1C)C)C
Properties
C9H12
Molar mass 120.19 g/mol
AppearanceColorless liquid
Density 0.8761 g/cm3
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)
-101.6·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H226, H315, H319, H332, H335, H411
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% [2]
NIOSH (US health exposure limits):
PEL (Permissible)
none [2]
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 [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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. [3]

In 1862, Warren De la Rue and Hugo Müller (1833-1915) proposed the term pseudocumole for the fractions heavier than xylole. [4]

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. [5]

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. [6]

In the next year, Fittig et al. adopted the pseudocumol terminology, [7] 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, [8] and in 1886 Oscar Jacobsen  [ de ] showed that the third trimethylbenzene he discovered earlier is also present. [9]

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. [10]

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. [11]

Scintillator

1,2,4-Trimethylbenzene dissolved in mineral oil is used as a liquid scintillator [12] in particle physics experiments such as NOνA and Borexino.

See also

Related Research Articles

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

<span class="mw-page-title-main">Styphnic acid</span> Chemical compound

Styphnic acid, or 2,4,6-trinitro-1,3-benzenediol, is a yellow astringent acid that forms hexagonal crystals. It is used in the manufacture of dyes, pigments, inks, medicines, and explosives such as lead styphnate. It is itself a low-sensitivity explosive, similar to picric acid, but explodes upon rapid heating.

The Fritsch–Buttenberg–Wiechell rearrangement, named for Paul Ernst Moritz Fritsch (1859–1913), Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl-alkyne by reaction with a strong base such as an alkoxide.

<span class="mw-page-title-main">Cyclopentene</span> Organic compound; 5-sided hydrocarbon ring

Cyclopentene is a chemical compound with the formula (CH2)3(CH)2. It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%. It is one of the principal cycloalkenes.

<span class="mw-page-title-main">Wilhelm Rudolph Fittig</span> German chemist (1835–1910)

Wilhelm Rudolph Fittig was a German chemist. He discovered the pinacol coupling reaction, mesitylene, diacetyl and biphenyl. Fittig studied the action of sodium on ketones and hydrocarbons. He discovered the Fittig reaction or Wurtz–Fittig reaction for the synthesis of alkylbenzenes, he proposed a diketone structure for benzoquinone and isolated phenanthrene from coal tar. He discovered and synthesized the first lactones and investigated structures of piperine, naphthalene, and fluorene.

The Lossen rearrangement is the conversion of a hydroxamate ester to an isocyanate. Typically O-acyl, sulfonyl, or phosphoryl O-derivative are employed. The isocyanate can be used further to generate ureas in the presence of amines or generate amines in the presence of H2O.

<i>Liebigs Annalen</i> Academic journal

Justus Liebig's Annalen der Chemie was one of the oldest and historically most important journals in the field of organic chemistry worldwide. It was established in 1832 and edited by Justus von Liebig with Friedrich Wöhler and others until Liebig's death in 1873. The journal was originally titled Annalen der Pharmacie; its name was changed to Justus Liebig's Annalen der Chemie in 1874. In its first decades of publishing, the journal was both a periodical containing news of the chemical and pharmaceutical fields and a publisher of primary research. During this time, it was noted to contain rebuttals and criticism of the works it published, inserted by Justus von Liebig during his tenure as an editor. After 1874, changes were made to editorial policies, and the journal published only completed research; later on, in the 20th century, its focus was narrowed to only print articles on organic chemistry, though it had always placed emphasis on the field. The journal was especially influential in the mid-19th century, but by the post-World War II period was considered "no longer as preeminent as it once was".

The Wurtz–Fittig reaction is the chemical reaction of an aryl halide, alkyl halides, and sodium metal to give substituted aromatic compounds. Following the work of Charles Adolphe Wurtz on the sodium-induced coupling of alkyl halides, Wilhelm Rudolph Fittig extended the approach to the coupling of an alkyl halide with an aryl halide. This modification of the Wurtz reaction is considered a separate process and is named for both scientists.

The Thorpe reaction is a chemical reaction described as a self-condensation of aliphatic nitriles catalyzed by base to form enamines. The reaction was discovered by Jocelyn Field Thorpe.

The Bunsen reaction is a chemical reaction that describes water, sulfur dioxide, and iodine reacting to form sulfuric acid and hydrogen iodide:

<span class="mw-page-title-main">Pyranine</span> Chemical compound

Pyranine is a hydrophilic, pH-sensitive fluorescent dye from the group of chemicals known as arylsulfonates. Pyranine is soluble in water and has applications as a coloring agent, biological stain, optical detecting reagent, and a pH indicator. Pyranine is also used in yellow highlighters to provide their characteristic fluorescence and bright yellow-green colour. It is also found in some types of soap.

<span class="mw-page-title-main">Hugo Erdmann</span> German chemist (1862–1910)

Hugo Wilhelm Traugott Erdmann was the German chemist who discovered, together with his doctoral advisor Jacob Volhard, the Volhard-Erdmann cyclization. In 1898 he was the first who coined the term noble gas.

<span class="mw-page-title-main">Mellitic anhydride</span> Chemical compound

Mellitic anhydride, the anhydride of mellitic acid, is an organic compound with the formula C12O9.

<span class="mw-page-title-main">4-Phenyl-1,2,4-triazole-3,5-dione</span> Chemical compound

4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) is an azodicarbonyl compound. PTAD is one of the strongest dienophiles and reacts rapidly with dienes in Diels-Alder reactions. The most prominent use of PTAD was the first synthesis of prismane in 1973.

1,2,3-Trimethylbenzene is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid. It is nearly insoluble in water but soluble in organic solvents.

<span class="mw-page-title-main">5-Aminotetrazole</span> Chemical compound

5-Aminotetrazole is an organic compound with the formula HN4CNH2. It is a white solid that can be obtained both in anhydrous and hydrated forms.

<span class="mw-page-title-main">Nitrotriazolone</span> Chemical compound

Nitrotriazolone (NTO) is a heterocyclic ketone high explosive first identified in 1905, but research into its explosive properties was not conducted until the 1980s. NTO is currently being used by the US Army in munitions, specifically Insensitive munitions replacing those made with legacy explosives.

The Nef isocyanide reaction is an addition reaction that takes place between isocyanides and acyl chlorides to form imidoyl chloride products, a process first discovered by John Ulrich Nef.

<span class="mw-page-title-main">Cyameluric acid</span> Chemical compound

Cyameluric acid or 2,5,8-trihydroxy-s-heptazine is a chemical compound with formula C
6
N
7
O
3
H
3
, usually described as a heptazine molecule with the hydrogen atoms replaced by hydroxyl groups –OH; or any of its tautomers.

<span class="mw-page-title-main">August Bernthsen</span> German chemist

Heinrich August Bernthsen was a German chemist who was among the first to synthesize and study the structures of methylene blue and phenothiazine.

References

  1. Merck Index , 11th Edition, 7929
  2. 1 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.