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47675

Sigma-Aldrich

Formaldehyde diethyl acetal

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

Synonym(s):

Diethoxymethane, Ethylal

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About This Item

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

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%)

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.)

SMILES string

CCOCOCC

InChI

1S/C5H12O2/c1-3-6-5-7-4-2/h3-5H2,1-2H3

InChI key

KLKFAASOGCDTDT-UHFFFAOYSA-N

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General description

Formaldehyde diethyl acetal (FDEA, diethoxymethane, DEM) is a diethyl acetal. It has been synthesized from ethanol and aqueous formaldehyde. 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. Its condensation with 2-propylresorcinol to form resorcin[n]arenes (n=4–7) has been investigated. The IR and Raman spectra and conformations of DEM have been studied. NMR spectroscopy has been used to study the aggregation behavior of organolithium compounds in diethoxymethane. Unimolecular metastable decomposition of DEM upon electron impact has been studied. Solubility of non-polar gases in DEM has been evaluated.

Application

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

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

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

Certificates of Analysis (COA)

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Solubility of non polar gases in formaldehyde diethyl acetal between-10 and 30?C, and 1 Atm partial pressure of gas.
Lizano LP, et al.
Journal of Solution Chemistry, 19(7), 721-728 (1990)
NMR spectroscopy of organolithium compounds, Part XVI: The aggregation behavior of butyllithium, phenyllithium, and lithium diisopropylamide in dimethoxy-and diethoxymethane.
Bergander K, et al.
Tetrahedron, 50(20), 5861-5868 (1994)
Sc(OTf)3-catalyzed cyclocondensation of 2-propylresorcinol with diethoxymethane. Formation and fragmentation of resorcin [n] arenes.
Morikawa O, et al.
Tetrahedron Letters, 45(29), 5731-5734 (2004)
Use of Diethoxymethane as a Solvent for Phase-Transfer Esterification of Carboxylic Acids.
Coleman MT.
Synthetic Communications, 42(13), 1911-1913 (2012)
Reaction of ethanol and formaldehyde: use of versatile cation-exchange resins as catalyst in batch reactors and reactive distillation columns.
Chopade SP and Sharma MM.
Reactive functional Polymers, 32(1), 53-65 (1997)
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