1,2,3-Trimethylbenzene

Last updated
1,2,3-Trimethylbenzene
Hemellitol.svg
1,2,3-Trimethylbenzene-3D-balls.png
Names
Preferred IUPAC name
1,2,3-Trimethylbenzene
Other names
Hemellitol; Hemimellitol, Hemimelithol; Hemimellitine; Hemimellitene
Identifiers
3D model (JSmol)
1903410
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.633 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-394-8
326517
PubChem CID
RTECS number
  • DC3300000
UNII
UN number 1993
  • InChI=1S/C9H12/c1-7-5-4-6-8(2)9(7)3/h4-6H,1-3H3 Yes check.svgY
    Key: FYGHSUNMUKGBRK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C9H12/c1-7-5-4-6-8(2)9(7)3/h4-6H,1-3H3
  • c1(cccc(c1C)C)C
Properties
C9H12
Molar mass 120.195 g·mol−1
AppearanceColorless liquid [1]
Density 0.89 g/mL [1]
Melting point −25 °C (−13 °F; 248 K) [1]
Boiling point 176 °C (349 °F; 449 K) [1]
0.006% (20°C) [2]
Vapor pressure 1 mmHg (16.7°C) [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable [3]
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H226, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 11 °C; 51 °F; 284 K [1]
243 °C; 470 °F; 516 K [1]
Explosive limits 0.8%-6.6% [2]
NIOSH (US health exposure limits):
PEL (Permissible)
none [2]
REL (Recommended)
TWA 25 ppm (125 mg/m3) [2]
IDLH (Immediate danger)
N.D. [2]
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 ?)

1,2,3-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.

The compound occurs naturally in coal tar and petroleum. It is one of the three isomers of trimethylbenzene. It is used in jet fuel, mixed with other hydrocarbons, to prevent the formation of solid particles which might damage the engine.

German chemist Oscar Jacobsen  [ de ] first prepared the hydrocarbon in 1882 and designated it hemellitol as a reference to the trivial name of hexamethylbenzene. [4] Four years later he also discovered it in the coal tar. [5]

Production

Industrially, it is isolated from the C9 aromatic hydrocarbon fraction during petroleum distillation. It is also generated by methylation of toluene and xylenes. [6]

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.

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

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

Stibine (IUPAC name: stibane) is a chemical compound with the formula SbH3. A pnictogen hydride, this colourless, highly toxic gas is the principal covalent hydride of antimony, and a heavy analogue of ammonia. The molecule is pyramidal with H–Sb–H angles of 91.7° and Sb–H distances of 170.7 pm (1.707 Å). The smell of this compound from usual sources (like from reduction of antimony compounds) is reminiscent of arsine, i.e. garlic-like.

The Bischler–Möhlau indole synthesis, also often referred to as the Bischler indole synthesis, is a chemical reaction that forms a 2-aryl-indole from an α-bromo-acetophenone and excess aniline; it is named after August Bischler and Richard Möhlau .

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Friedrich Karl Johannes Thiele was a German chemist and a prominent professor at several universities, including those in Munich and Strasbourg. He developed many laboratory techniques related to isolation of organic compounds. In 1907 he described a device for the accurate determination of melting points, since named Thiele tube after him.

<span class="mw-page-title-main">Indene</span> Bicyclic hydrocarbon compound with formula C9H8

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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.

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<span class="mw-page-title-main">Alexander Naumann</span>

Alexander Nikolaus Franz Naumann was a Prussian and German physical chemist and a professor at the University of Giessen. He was a pioneer of chemical thermodynamics and proposed that molecules reacted when their energy levels exceeded a certain critical level which could be achieved through the provision of heat.

<span class="mw-page-title-main">Karl Reimer</span> German chemist and industrialist

Karl Ludwig Reimer was a German chemist and industrialist. He's responsible for the cheap synthesis of the chemical compound Vanillin, having discovered the Reimer-Tiemann Reaction.

References

  1. 1 2 3 4 5 6 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0637". National Institute for Occupational Safety and Health (NIOSH).
  3. CDC - NIOSH Pocket Guide to Chemical Hazards
  4. Jacobsen, Oscar (1882). "Ueber Isodurol, Isodurylsäuren und das dritte Trimethylbenzol". Berichte der deutschen chemischen Gesellschaft. 15 (2): 1853–1858. doi:10.1002/cber.18820150292. ISSN   0365-9496.
  5. 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.
  6. 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