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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-H319-H335
Highly flammable liquid and vapour. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P337+P313-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. Avoid breathing 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 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. If eye irritation persists: Get medical advice/attention. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant