Dimethoxymethane

Dimethoxymethane
Dimethoxymethane
Identifiers
CAS number 109-87-5 YesY
PubChem 8020, 10080321 (2H3)methoxy, 18424407 sulfane, 21424378 methoxymethane
ChemSpider 13837190 YesY, 8255859 (2H3)methoxy YesY
EC number 203-714-2
UN number 1234
MeSH Dimethoxymethane
ChEBI CHEBI:48341
ChEMBL CHEMBL15537 YesY
RTECS number PA8750000
Beilstein Reference 1697025
Gmelin Reference 100776
Jmol-3D images Image 1
Properties
Molecular formula C3H8O2
Molar mass 76.09 g mol−1
Exact mass 76.052429500 g mol-1
Appearance Colorless liquid
Density 0.860 g cm-3 (at 20 °C)
Melting point

-104.8 °C, 168 K, -157 °F

Boiling point

42 °C, 315 K, 108 °F

Hazards
EU classification Flammable (F)
Irritant (Xi)
R-phrases R11 R36/37/38
S-phrases S9, S16, S33
Flash point -18 °C
Related compounds
Related Ethers Dimethoxyethane
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dimethoxymethane, also called methylal, is a clear colorless flammable liquid with a low boiling point, low viscosity and an excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.

It can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol. In aqueous acid, it is hydrolyzed back to formaldehyde and methanol.

It is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings.

Another useful application of dimethoxymethane is to protect alcohols with a MOM ether in organic synthesis. This can be done using phosphorus pentoxide in dry dichloromethane or chloroform. This is a preferred method to using MOM-Cl. The MOM-ether can be removed using methanol and pToluene Sulphonic Acid as an alternative to aqueous acid. Due to the anomeric effect, dimethoxymethane has a preference toward the gauche conformation around the C–O bonds, instead of the anti conformation. Since it is one of the smallest molecules exhibiting this effect, which has great interest in carbohydrate chemistry, dimethoxymethane is often used for theoretical studies of the anomeric effect.

References

  • Merck Index, 11th Edition, 5936

External links


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Look at other dictionaries:

  • dimethoxymethane — /duy meuh thok see meth ayn/, n. Chem. methylal. [DI 1 + METH(YL) + OXY 2 + METHANE] * * * …   Universalium

  • dimethoxymethane — noun A clear colourless flammable liquid with a low boiling point, low viscosity, and excellent dissolving power, the dimethyl acetal of formaldehyde. Syn: methylal …   Wiktionary

  • dimethoxymethane — /ˌdaɪmɛθɒksiˈmiθeɪn/ (say .duymethoksee meethayn) noun → methylal. {di 1 + meth(yl) + oxy(gen) + methane} …  

  • dimethoxymethane — /duy meuh thok see meth ayn/, n. Chem. methylal. [DI 1 + METH(YL) + OXY 2 + METHANE] …   Useful english dictionary

  • Liste de mélanges azéotropes — Cette liste répertorie des solvants qui forment des mélanges azéotropes. Azéotropes binaires[1] solvant A pourcentage molaire A solvant B pourcentage molaire B température d ébullition 1,1 dichloroéthane 71,36 méthanol 28,64 322.25 …   Wikipédia en Français

  • Acetal — For the plastic, see Polyoxymethylene plastic. Not to be confused with Acetyl. Structure of a generic acetal …   Wikipedia

  • Formal — The term formal has a number of uses, including:General*relating to formality *opposite of informalocial* Formal occasion ** Formal attire worn on such occasions ** Formals are particular meals at some British universities ** In Australian or… …   Wikipedia

  • Dimethoxyethane — Glyme redirects here. For the river in Oxfordshire, England, see River Glyme. Dimethoxyethane IUPAC name …   Wikipedia

  • DMM — may refer to: Contents 1 Companies 2 Publications 3 Science and technology 4 People 5 Other …   Wikipedia

  • Anomeric effect — In organic chemistry, the anomeric effect or Edward Lemieux effect is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to a heteroatom within a cyclohexane ring to prefer the axial orientation instead of …   Wikipedia

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