Dimethoxymethane 5156882 221401346 2008-06-24T10:19:05Z Tomaxer 3686472 Added links and information to chembox {{Chembox new | ImageFile = Dimethoxymethane-2D-skeletal.png | ImageFile1 = Dimethoxymethane-gauche-gauche-conformer-3D-balls.png | IUPACName = Dimethoxymethane | OtherNames = Methylal; formal; formaldehyde dimethyl ether | Section1 = {{Chembox Identifiers | CASNo = 109-87-5 | EINECS = 203-714-2 | PubChem = | SMILES = COCOC | RTECS = PA8750000 }} | Section2 = {{Chembox Properties | Formula = C<sub>3</sub>H<sub>8</sub>O<sub>2</sub> | MolarMass = 76.1 g/mol | Appearance = Colorless liquid | Density = 0.860 g/mL | MeltingPt = -104.8 &deg;C | BoilingPt = 42.3 &deg;C | Solubility = }} | Section7 = {{Chembox Hazards | ExternalMSDS = | EUClass = Flammable ('''F''')<br />Irritant ('''Xi''') | RPhrases = {{R11}} {{R36/37/38}} | SPhrases = {{S9}}, {{S16}}, {{S33}} | FlashPt = -18 °C }} | Section8 = {{Chembox Related | Function = [[Ether]]s | OtherFunctn = [[Dimethoxyethane]] | OtherCpds = }} }} '''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 [[hydrolysis|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. Due to the [[anomeric effect]], dimethoxymethane has a preference toward the ''gauche'' [[conformational isomerism|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== * {{ICSC|1152|11}} * {{PGCH|0396}} * [http://msds.chem.ox.ac.uk/ME/methylal.html MSDS at Oxford University] [[Category:Ethers]] [[Category:Acetals]] [[Category:Ether solvents]] [[de:Dimethoxymethan]] [[nl:Dimethoxymethaan]]