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Merck
CN

47675

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57651078
EC Number:
207-330-6
Beilstein/REAXYS Number:
1697253
MDL number:
MFCD00009246
Assay:
≥99.0% (GC)
Technique(s):
GC/GC: suitable
Bp:
87-88 °C (lit.)
Vapor pressure:
60 mmHg ( 25 °C)

Key Documents

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Product Name

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

InChI key

KLKFAASOGCDTDT-UHFFFAOYSA-N

InChI

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

SMILES string

CCOCOCC

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

Quality Level

100

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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.

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.

pictograms

Flame
GHS02

signalword

Danger

hcodes

H225

Hazard Classifications

Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

23.0 °F - closed cup

flash_point_c

-5 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
STBK6118
STBK5627
STBK3428
STBJ8739
STBH9540

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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)
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)
Metastable decompositions of gem-dialkoxyalkanes upon electron impact. III. Diethoxymethane (CH2 (OCH2CH3)2).
Tajima S, et al.
Rapid Communications in Mass Spectrometry, 14(14), 1195-1199 (2000)
Study on the synthesis of diethoxy methane using toluene-p-sulfonic acid as catalyst.
Gu Z, et al.
Chinese Journal of Applied Chemistry / Ying Yong Hua Xue, 22(12), 1368-1368 (2005)
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