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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-H304-H315-H319-H335-H336
Flammable liquid and vapour. May be fatal if swallowed and enters airways. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May cause drowsiness or dizziness.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P280-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P312-P314-P331-P332+P313-P337+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. Get medical advice/attention if you feel unwell. Do NOT induce vomiting. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant