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Trimethyl orthoformate is used as a protecting group for aldehydes in organic synthesis, as an additive in polyurethane coatings and as a dehydrating agent in the preparation of surface modified colloidal silica nanoparticles. It is also used as a chemical intermediate in the preparation of vitamin B1 and sulfa drugs. It acts as an effective solvent for thallium(III) nitrate-mediated oxidations. Furthermore. It is utilized for the synthesis of chromone from keto-hydroxy naphthol in the presence of trimethylamine.
Reagent for the acid-catalyzed conversion of ketones to their methyl enol ethers in good yield: Synthesis, 38 (1974). For an example, see: Org. Synth. Coll., 8, 357 (1993).
Protects the cis-2,3-diol system of ribonucleosides as their methoxymethylene acetals (cyclic orthoformates), readily hydrolyzed by mild acid: Synthesis, 408 (1985).
In the presence of HCl, is an alternative to formic acid in the synthesis of benzoxazoles from ortho-amino phenols: Org. Prep. Proced. Int., 22, 613 (1990).
For further reactions of alkyl orthoformates, see Triethyl orthoformate, A13587.
Nemeth, I.; Kiss-Szikszai, A.; Illyes, T. Z.; Mandi, A.; Komaromi, I.; Kurtan, T.; Antus, S. Oxidative Rearrangement of Flavanones with Thallium(III) Nitrate, Lead Tetraacetate and Hypervalent Iodines in Trimethyl Orthoformate and Perchloric or Sulfuric Acid. Z. Naturforsch. B Chem. Sci. 2012, 67B (12), 1289-1296.
Pospech, J.; Lennox, A. J.; Beller, M. Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres. Chem. Commun. 2015, 51 (77), 14505-14508.
Hazard Statements: H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.