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47649

Sigma-Aldrich

Formaldehyde dimethyl acetal

for Grignard reactions, ≥99.0% (GC)

Synonym(s):

Dimethoxymethane, Methylal

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About This Item

Linear Formula:
CH2(OCH3)2
CAS Number:
Molecular Weight:
76.09
Beilstein:
1697025
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

≥99.0% (GC)

reaction suitability

reaction type: Grignard Reaction

impurities

≤0.2% water

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 ampiphilic 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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 2

Supplementary Hazards

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
An efficient protocol for the preparation of MOM ethers and their deprotection using zirconium (IV) chloride.
Sharma GVM, et al.
Tetrahedron Letters, 45(50), 9229-9232 (2004)
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)
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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