Used to protect diols as their methylene acetals, using TMS-OTf/2,6-lutidine:
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Used to protect diols as their methylene acetals, using TMS-OTf/2,6-lutidine:
Solubility
Soluble in water 20°C 330g/L.
Notes
Moisture Sensitive. Store away from oxidizing agents, moisture/water and acids. Store under inert gas.
RUO – Research Use Only
General References:
- 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); Iodotrimethyl silane, 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).