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Mesitylene is used to make plastics and dyes. It acts as a solvent, ligand in organometallic chemistry and precursor to 2,4,6-trimethylaniline. It is also used as a developer for photopatternable silicones due to its solvent properties in the electronics industry. It is used as an internal standard in nuclear magnetic resonance (NMR) samples due to the presence of three equivalent protons in it. It is involved in the production of trimesic acid and antioxygen, epoxy firming agent and polyester resin stabilizers. Further, it is used as an additive and component in aviation gasoline blends.
The Adams modification of the Gattermann reaction for aromatic formylation by reaction with Zinc cyanide, L15836 , and HCl is exemplified: Org. Synth. Coll., 3, 549 (1955). The Vilsmeier formylation (see N,N-Dimethylformamide, A13547 ), has been extended to less activated substrates, including mesitylene, by use of the combination of DMF and triflic anhydride: J. Chem. Soc., Chem. Commun., 1571 (1990).
For conversion to mesitoic acid by Friedel-Crafts reaction with oxalyl chloride, and aqueous work-up, see: Org. Synth. Coll., 5, 706 (1973).
Singh, P. Synthesis of mesitylene-based polyamine dendrimer for functionalisation of single-walled carbon nanotubes. J. Exp. Nanosci. 2015, 10 (6), 429-437.
Medina, D. D.; Rotter, J. M.; Hu, Y.; Dogru, M.; Werner, V.; Auras, F.; Markiewicz, J. T.; Knochel, P.; Bein, T. Room Temperature Synthesis of Covalent-Organic Framework Films through Vapor-Assisted Conversion. J. Am. Chem. Soc. 2015, 137 (3), 1016-1019.
Hazard Statements: H226-H335
Flammable liquid and vapour. May cause respiratory irritation.
Precautionary Statements: P210-P261-P280a-P303+P361+P353-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.