Mesitylene

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Mesitylene
Mesitylene Mesitylene
Identifiers
CAS number 108-67-8 YesY
PubChem 7947
ChemSpider 7659 YesY
EC number 203-604-4
KEGG C14508 YesY
ChEBI CHEBI:34833 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H12
Molar mass 120.19 g/mol
Density 0.8637 g/cm³ at 20 °C
Melting point −44.8 °C
Boiling point 164.7 °C
Structure
Dipole moment 0.047 D [1]
Hazards
MSDS Safety data from Sigma Aldrich
Flash point 50 °C[2]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents symmetrically placed on the ring. Isomeric trimethylbenzenes include 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 colourless 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.[3]

Preparation[edit]

Mesitylene is prepared by equilibration of xylene (or simple methyl alkylation of it) over solid acid catalyst:[3]

2 C6H4(CH3)2 ⇌ C6H3(CH3)3 + C6H5CH3
C6H4(CH3)2 + CH3OH → C6H3(CH3)3 + H2O

Although impractical, it could be prepared by trimerization of propyne, also requiring an acid catalyst, affords a mixture of 1,3,5- and 1,2,4-trimethylbenzenes.

Catalyzing and dehydrating by sulfuric acid, trimerization of acetone via aldol condensation also affords mesitylene.

Reactions[edit]

Oxidation of mesitylene with nitric acid affords trimesic acid ( C6H3(CO2H)3). Using the milder oxidant manganese dioxide, one obtains 3,5- dimethylbenzaldehyde. With metal centers it functions as a ligand, one example being (η6-C6H3Me3)Mo(CO)3.[4]

Applications[edit]

Mesitylene is mainly used as a precursor to 2,4,6-trimethylaniline, a precursor to colorants. This derivative is prepared by selective mononitration of mesitylene, avoiding oxidation of the methyl groups.[5]

Niche uses[edit]

in the laboratory mesitylene is a specialty solvent. It also serves as a ligand in organometallic chemistry, one example being (η6-C6H3Me3)Mo(CO)3.

In the electronics industry, mesitylene has also been used as a developer for photopatternable silicones due to its solvent properties.

The three aromatic hydrogen atoms of mesitylene are in identical chemical shift environments. Therefore, they only give a single peak near 6.8 ppm in the 1H NMR spectrum. For this reason, mesitylene is sometimes used as an internal standard in NMR samples that contain aromatic protons.[6]

History[edit]

Mesitylene was first prepared in 1837 by Robert Kane, an Irish chemist, by heating acetone with concentrated sulfuric acid.[7] He named his new substance "mesitylene" because the German chemist Carl Reichenbach had named acetone "mesit" (from the Greek μεσίτης, the mediator),[8] and Kane believed that his reaction had dehydrated mesit, converting it to an alkene, "mesitylene".[9] However, Kane's determination of the chemical composition ("empirical formula") of mesitylene was incorrect. The correct empirical formula was provided by August W. von Hofmann in 1849.[10] In 1866 Adolf von Baeyer showed that mesitylene's structure was consistent with that of 1,3,5-trimethylbenzene;[11] however, conclusive proof that mesitylene was identical to 1,3,5-trimethylbenzene was provided by Albert Ladenburg in 1874.[12]

Mesityl group[edit]

The group (CH3)3C6H2- is called mesityl. Mesityl derivatives, e.g. tetramesityldiiron, are typically prepared from the Grignard reagent (CH3)3C6H2MgBr.

Safety and the environment[edit]

Mesitylene is also a major urban volatile organic compound (VOC) which results from combustion. It plays a significant role in aerosol and tropospheric ozone formation as well as other reactions in atmospheric chemistry.


References[edit]

  1. ^ Zhao, Jun; Zhang, Renyi (2004). "Proton transfer reaction rate constants between hydronium ion (H3O+) and volatile organic compounds". Atmospheric Environment 38 (14): 2177–2185. doi:10.1016/j.atmosenv.2004.01.019. 
  2. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  3. ^ a b 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.
  4. ^ Girolami, G. S.; Rauchfuss, T. B. and Angelici, R. J., Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA, 1999. ISBN 0-93570248-2.
  5. ^ Gerald Booth "Nitro Compounds, Aromatic" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_411
  6. ^ http://chemicalland21.com/industrialchem/organic/MESITYLENE.htm
  7. ^ Robert Kane (1839) "On a series of combinations derived from pyroacetic spirit [acetone]" Transactions of the Royal Irish Academy, vol. 18, pages 99–125.
  8. ^ Reichenbach's research is excerpted in: C. Reichenbach (1834) "Ueber Mesit (Essiggeist) und Holzgeist" (On mesit (spirit of vinegar) and wood spirits), Annalen der Pharmacie, vol. 10, no. 3, pages 298–314.
  9. ^ For an explanation of the original of the name "mesitylene", see also: Henry E. Roscoe, A Treatise on Chemistry (New York, New York: D. Appleton and Co., 1889), vol. III, page 102, footnote 2.
  10. ^ A.W. Hofmann (1849) "On the composition of mesitilole [mesitylene], and some of its derivatives", The Quarterly Journal of the Chemical Society of London, vol. 2, pages 104–115. (Note: The empirical formula of mesitylene as stated in Hofmann's paper ( C18H12 ) is incorrect; however, this happened because Hofmann used 6 as the atomic weight of carbon, instead of the correct atomic weight of 12. Once the correct atomic weight is used in Hofmann's calculations, his results give the correct empirical formula of C9H12.)
  11. ^ Adolf von Baeyer (1866) "Ueber die Condensationsproducte des Acetons" (On condensation products of acetone), Annalen der Chemie und Pharmacie, vol. 140, pages 297–306.
  12. ^ Albert Ladenburg (1874) "Ueber das Mesitylen" (On mesitylene), Berichte der deutschen chemischen Gesellschaft, vol. 7, pages 1133–1137. doi: 10.1002/cber.18740070261