47675

Formaldehyde diethyl acetal

absolute, over molecular sieve (H₂O ≤0.01%), ≥99.0% (GC)

• Synonym(s): Diethoxymethane, Ethylal
• Linear Formula: CH₂(OC₂H₅)₂
• CAS Number: 462-95-3
• Molecular Weight: 104.15
• Beilstein: 1697253
• EC Number: 207-330-6
• MDL number: MFCD00009246
• UNSPSC Code: 12352100
• PubChem Substance ID: 57651078
• NACRES: NA.22
• Assay: ≥99.0% (GC)
• Technique(s): GC/GC: suitable
• Bp: 87-88 °C (lit.)
• Vapor pressure: 60 mmHg ( 25 °C)

Properties

• vapor density: 3.6 (vs air)
• vapor pressure: 60 mmHg ( 25 °C)
• grade: absolute
• Assay: ≥99.0% (GC)
• form: liquid
• autoignition temp.: 346 °F
• quality: over molecular sieve (H₂O ≤0.01%)
• technique(s): GC/GC: suitable
• refractive index: n20/D 1.373 (lit.); n20/D 1.374
• bp: 87-88 °C (lit.)
• density: 0.831 g/mL at 25 °C (lit.)
• functional group: ether
• SMILES string: CCOCOCC
• InChI: 1S/C5H12O2/c1-3-6-5-7-4-2/h3-5H2,1-2H3
• InChI key: KLKFAASOGCDTDT-UHFFFAOYSA-N

Description

General description

Formaldehyde diethyl acetal (FDEA, diethoxymethane, DEM) is a diethyl acetal. It has been synthesized from ethanol and aqueous formaldehyde.[1][2] It is a low boiling solvent useful for sodium hydride reactions, organolithium chemistry, copper-catalyzed conjugate additions and phase-transfer reactions. It is a potential alternate for tetrahydrofuran, dichloromethane, glyme and methylal. DEM is an ethoxymethylating agent, a formaldehyde equivalent and a carbonylation substrate.[3] Its condensation with 2-propylresorcinol to form resorcin[n]arenes (n=4–7) has been investigated.[4] The IR and Raman spectra[5] and conformations of DEM have been studied.[6] NMR spectroscopy has been used to study the aggregation behavior of organolithium compounds in diethoxymethane.[7] Unimolecular metastable decomposition of DEM upon electron impact has been studied.[8] Solubility of non-polar gases in DEM has been evaluated.[9]

Application

Formaldehyde diethyl acetal may be used as a solvent in the esterification of carboxylic acids[10] and in the O-alkylation of a variety of phenols.[11]

Safety Information

• Pictograms: GHS02
• Signal Word: Danger
• Hazard Statements: H225
• Precautionary Statements: P210 - P233 - P240 - P241 - P242 - P243
• Hazard Classifications: Flam. Liq. 2
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 1
• Flash Point(F): 23.0 °F - closed cup
• Flash Point(C): -5 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves