Dimethoxymethane

• Catalog No.: A12055
• CAS Number: 109-87-5
• M. F.: C3H8O2
• M. W.: 76.09442
• Purity: 98%

SYNONYMS

• Title: 二甲氧基甲烷
• IUPAC name: dimethoxymethane
• IUPAC Traditional name: dimethoxymethane
• Synonyms: Methylal; Formaldehyde dimethyl acetal

DATABASE IDS

• EC Number: 203-714-2
• MDL Number: MFCD00008495
• Merck Index: 146012
• CAS Number: 109-87-5
• Beilstein Number: 1697025

PROPERTIES

• Purity: 98%
• Boiling Point: 41-42°C
• Density: 0.863
• Flash Point: -17°C(1°F)
• Melting Point: -105°C
• Refractive Index: 1.3545
• GHS Hazard statements: H225-H319
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P403+P235-P501A
• Risk Statements: 11-36
• RTECS: PA8750000
• Safety Statements: 9-16-26
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1234
• Packing Group: II

REFERENCES

• 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).
• Formaldehyde equivalent and low-toxicity solvent for non-acidic materials.
• Can be used in combination with n-hexanoyl chloride for the generation of chloromethyl methyl ether (caution!): J. Org. Chem., 59, 6499 (1994).