Dimethoxymethane

Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 414426643
|ImageFile = Dimethoxymethane 2D skeletal. png
|ImageName = Structural formula of dimethoxymethane
|ImageFile1 = Dimethoxymethane gauche gauche conformer 3D balls. png
|ImageName1 = Ball and stick model of dimethoxymethane
|PIN = Dimethoxymethane
|OtherNames = Formal
Formaldehyde dimethyl ether
Methylal
Dimethylformal (DMFL)
Formaldehyde dimethylacetal
Methoxymethyl methyl ether
Methylene dimethyl ether
|Section1=
|Section2=Chembox Properties
|C=3 | H=8 | O=2
|Appearance = Colorless liquid
|Odor = Chloroform like
|BoilingPtC = 42
|BoilingPt ref =
|ExploLimits = 2.2–13.8%
|LC50 = 18000 ppm (mouse, 7 hr)15000 ppm (rat)18354 ppm (mouse, 7 hr) 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.

Industrially, it is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings. Another application is as a gasoline additive for increasing octane number. Dimethoxymethane can also be used for blending with diesel.

Another useful application of dimethoxymethane is to protect alcohols with a methoxymethyl (MOM) ether in organic synthesis. Dimethoxymethane can be activated with phosphorus pentoxide in dichloromethane or chloroform. This method is preferred to the use of chloromethyl methyl ether (MOMCl). Phenols can also be MOM protected using dimethoxymethane, p toluenesulfonic acid. Alternatively, MOMCl can be generated as a solution by treating dimethoxymethane with an acyl chloride in the presence of a Lewis acid catalyst like zinc bromide:

MeOCH2OMe + RC(=O)Cl → MeOCH2Cl + RC(=O)(OMe)). Unlike the classical procedure, which uses formaldehyde and hydrogen chloride as starting materials, the highly carcinogenic side product bis(chloromethyl) ether is not generated.