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538280

Sigma-Aldrich

Diethoxymethane

99.7%, contains 50-150 ppm BHT as stabilizer

Synonym(s):

Formaldehyde diethyl acetal, 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:
12352112
PubChem Substance ID:
329758005
NACRES:
NA.21

vapor density

3.6 (vs air)

Quality Level

200

vapor pressure

60 mmHg ( 25 °C)

Assay

99.7%

form

liquid

autoignition temp.

346 °F

contains

50-150 ppm BHT as stabilizer

expl. lim.

8 %

refractive index

n20/D 1.373 (lit.)

bp

87-88 °C (lit.)

mp

-66.5 °C

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

Diethoxymethane (DEM) is a dialkoxymethane that can be synthesized by reacting ethanol and aqueous formaldehyde using macroporous cation-exchange resin Indion-130 as a catalyst. Infrared spectra of the conformers of DEM in various states have been obtained by matrix isolation infrared spectroscopy. The characteristic properties of DEM include low boiling point, low affinity for water, base stability and does not need drying for any reactions. Its infrared and Raman spectra have been reported.

Application

Diethoxymethane may be used as a substitute solvent to dichloromethane and toluene in the O-alkylation of different phenols in the presence of phase transfer catalysts (PTCs).

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

Certificates of Analysis (COA)

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Applications of diethoxymethane as a versatile process solvent and unique reagent in organic synthesis.
Boaz NW and Venepalli B.
Organic Process Research & Development, 5(2), 127-131 (2001)
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)
Use of Diethoxymethane as a Solvent for Phase Transfer-Catalyzed O-Alkylation of Phenols.
Coleman MT and LeBlanc G.
Organic Process Research & Development, 14(3), 732-736 (2010)
Infrared and Raman Spectra of Diethoxymethane and Diethoxymethane-d2.
Nukada K.
Bulletin of the Chemical Society of Japan, 34(11), 1624-1630 (1961)
Zhanna A Afonina et al.
Nucleic acids research, 43(1), 618-628 (2014-12-19)
Using sedimentation and cryo electron tomography techniques, the conformations of eukaryotic polyribosomes formed in a long-term cell-free translation system were analyzed over all the active system lifetime (20-30 translation rounds during 6-8 h in wheat germ extract at 25°C). Three
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