dimethoxymethane

• ChemBase ID: 127072
• Molecular Formular: C3H8O2
• Molecular Mass: 76.09442
• Monoisotopic Mass: 76.0524295
• SMILES: COCOC
• Canonical SMILES: COCOC
• InChI: InChI=1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3
• InChIKey: NKDDWNXOKDWJAK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethoxymethane
• IUPAC Traditional name: dimethoxymethane
• Synonyms: Formal; Formaldehyde dimethyl ether; Methylal; Dimethylformal (DMFL); Dimethoxymethane; Formaldehyde dimethyl acetal; Dimethoxymethane; Dimethoxymethane; Formaldehyde dimethyl acetal; 二甲醇缩甲醛; 二甲氧基甲烷; 二甲氧基甲烷; 甲缩醛; 二甲醇缩甲醛

Database IDs

• CAS Number: 109-87-5
• EC Number: 203-714-2
• MDL Number: MFCD00008495
• Beilstein Number: 1697025
• Merck Index: 146012
• PubChem SID: 162221395; 24893265; 24889145; 24871301; 24871262
• PubChem CID: 8020
• CHEBI ID: 48341
• CHEMBL: 15537
• Chemspider ID: 13837190
• Gmelin ID: 100776
• MeSH Name: Dimethoxymethane
• Wikipedia Title: Dimethoxymethane

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.18767487
• LogD (pH = 7.4): 0.18767487
• Log P: 0.18767487
• Molar Refractivity: 18.8655 cm^3
• Polarizability: 7.669779 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Melting Point: -104.8°C; -105 °C(lit.); -105°C
• Boiling Point: 41-42 °C(lit.); 41-42°C; 41-43 °C; 42°C
• Flash Point: -.4 °F; -17°C(1°F); -18 °C; -18 °C
• Auto Ignition Point: 459 °F
• Density: 0.86 g/mL at 25 °C(lit.); 0.860 g cm^-3 (at 20 °C); 0.860 g/mL at 20 °C(lit.); 0.863
• Refractive Index: 1.3545; n20/D 1.354; n20/D 1.354(lit.)
• Vapor Pressure: 6.38 psi ( 20 °C)
• Vapor Density: 2.6 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: PA8750000
• European Hazard Symbols: Flammable (F); Flammable (F); Irritant (Xi); Irritant (Xi)
• UN Number: 1234; UN1234
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-19-36; 11-36; R11 R36/37/38
• Safety Statements: 7/9-16-26-33; 9-16-26; S9, S16, S33
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• Explode Limits: 17.6 %
• GHS Hazard statements: H225-H319
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P403+P235-P501A; P210-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1234 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.

Product Information

• Purity: ≥90.0% (GC); ≥99.0% (GC); ≥99.5% (GC); 98%; 99%
• Grade: absolute; analytical standard; for Grignard reactions; ReagentPlus®; technical
• Impurities: ≤0.2% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality: over molecular sieve (H2O ≤0.01%)
• Linear Formula: CH2(OCH3)2

DETAILS

Sigma Aldrich - 47676

Packaging
250 mL in Sure/Seal™

Sigma Aldrich - 47649

Packaging
1 L in glass bottle
250 mL in glass bottle

Sigma Aldrich - 47650

Other Notes
Sales restrictions may apply

Sigma Aldrich - D134651

Packaging
1, 2, 2.5 L in glass bottle
18 L in steel drum
5, 100 mL in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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).