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Sigma-Aldrich

Formaldehyde dimethyl acetal

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

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Synonym(s):
Dimethoxymethane, Methylal
Linear Formula:
CH2(OCH3)2
CAS Number:
109-87-5
Molecular Weight:
76.09
Beilstein:
1697025
EC Number:
203-714-2
MDL number:
MFCD00008495
PubChem Substance ID:
57651079
NACRES:
NA.22

grade

absolute

Quality Level

100

Assay

≥99.0% (GC)

quality

over molecular sieve (H2O ≤0.01%)

refractive index

n20/D 1.354

density

0.860 g/mL at 20 °C (lit.)

SMILES string

COCOC

InChI

1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3

InChI key

NKDDWNXOKDWJAK-UHFFFAOYSA-N

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General description

Formaldehyde dimethyl acetal (FDA, FDMA, FADMA, dimethoxymethane, DMM, methylal) is a biodegradable dimethyl acetal. It has been synthesized by condensing formaldehyde with methanol in the presence of acid catalyst. It is amphiphilic in nature with low viscosity, surface tension and boiling point. It is a flammable, highly volatile solvent with excellent dissolving power. It is reported to form trimethylorthoformate by anodic methoxylation in basic methanol.

Application

Formaldehyde dimethyl acetal may be used in the following studies:
  • Synthesis of methoxymethyl (MOM) ethers.
  • As an external cross-linker to form microporous polymers.
  • Dehydration of biological samples for scanning electron microscopy (SEM).

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Hazard Classifications

Flam. Liq. 2

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-0.4 °F - closed cup

Flash Point(C)

-18 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Electrosynthesis of trimethylorthoformate on BDD electrodes.
Fardel R, et al.
J. Appl. Electrochem., 36(2), 249-253 (2006)
Calceolariaceae: floral development and systematic implications.
Mayr EM and Weber A.
American Journal of Botany, 93(3), 327-343 (2006)
A new strategy to microporous polymers: knitting rigid aromatic building blocks by external cross-linker.
Li B, et al.
Macromolecules, 44(8), 2410-2414 (2011)
Highly efficient and selective methoxymethylation of alcohols and phenols catalyzed by high-valent tin (IV) porphyrin.
Gharaati S, et al.
Inorgorganica Chimica Acta, 363(9), 1995-2000 (2010)
Jenn-Huei Lii et al.
Carbohydrate research, 340(5), 853-862 (2005-03-23)
The rotational barrier for a methyl group at the end of an anomeric system is sometimes lower than we might have anticipated. Thus, in the trans-trans conformation of dimethoxymethane, the barrier to methyl rotation is calculated (B3LYP/6-311++G(2d,2p)) to be 2.22
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