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Used to protect diols as their methylene acetals, using TMS-OTf/2,6-lutidine:
L A Tomilina.; Iu S Rotenberg.; F D Mashbits.; M B Komanovskaia.; L M Knizhnikova. Methylal: its metabolism and hygienic standardization in the air of work areas.Gig Tr Prof Zabol.1984,627-29.
Ronald J Gillespie.; Edward A Robinson.; Julien Pilmé. Ligand close packing, molecular compactness, the methyl tilt, molecular conformations, and a new model for the anomeric effect.Chemistry.2010,16(12), 3663-3675 .
Formaldehyde equivalent and low-toxicity solvent for non-acidic materials.
In combination with P2O5, protects alcohols as their methoxymethyl (MOM) ethers, usually preferable to methods using carcinogenic methoxymethyl halides: Synthesis, 276 (1975); Org. Synth. Coll., 9, 539 (1998). The MOM group is more effective than the methoxy group in the activation of aromatics to lithiation: Synthesis, 906 (1979). Alternative agents for promoting this acetal exchange include: BF3 etherate and 4A sieves: Org. Synth. Coll., 9, 704 (1998); tosic acid and molecular sieves: Synthesis, 244 (1976) or LiBr: Synthesis, 74 (1985), or tosic acid itself: Org. Prep. Proced. Int., 22, 63 (1990); Iodotrimethylsilane, A12902: Synthesis, 896 (1983); montmorillonite K 10: Indian J. Chem. B., 35B, 260 (1996); see also Scandium(III) trifluoromethanesulfonate hydrate, 40566. The MOM group is readily cleaved with mild acid, e.g. HCl: J. Chem. Soc., Chem. Commun., 298 (1974); J. Org. Chem., 40, 2025 (1975), PPTS: Synth. Commun., 13, 1021 (1983), TFA: J. Am .Chem. Soc., 103, 3210 (1981), Dowex 50WX2 resin: Synth. Commun., 22, 2823 (1983).
Has also been used to protect diols as their methylene acetals, using TMS-OTf/2,6-lutidine: Tetrahedron Lett., 26, 4639 (1985), or LiBr/TsOH: Tetrahedron Lett., 28, 6601 (1987).
Can be used in combination with n-hexanoyl chloride for the generation of chloromethyl methyl ether (caution!): J. Org. Chem., 59, 6499 (1994).
Gefahrenhinweise (EU): H225-H319
Highly flammable liquid and vapour. Causes serious eye irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. 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. Dispose of contents/container in accordance with local/regional/national/international regulations.