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{{distinguish|dimethoxyethane}}{{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 = FormalFormaldehyde dimethyl etherMethylalDimethylformal (DMFL)Formaldehyde dimethylacetalMethoxymethyl methyl etherMethylene dimethyl ether|Section1={{Chembox Identifiers|CASNo = 109-87-5

correct|CAS}}

correct|FDA}}|UNII = 7H1M4G2NUE|PubChem = 8020|ChemSpiderID = 13837190

correct|chemspider}}|EINECS = 203-714-2|UNNumber = 1234|MeSHName = Dimethoxymethane

correct|EBI}}|ChEBI = 48341|RTECS = PA8750000|SMILES = COCOC

correct|EBI}}|ChEMBL = 15537

correct|chemspider}}|StdInChI = 1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3|InChI = 1/C3H8O2/c1-4-3-5-2/h3H2,1-2H3

correct|chemspider}}|StdInChIKey = NKDDWNXOKDWJAK-UHFFFAOYSA-N|InChIKey = NKDDWNXOKDWJAK-UHFFFAOYAE|Beilstein = 1697025|Gmelin = 100776}}|Section2={{Chembox Properties

H=8 | O=2 |Appearance = Colorless liquidMerck Index, 11th Edition, 5936|Odor = Chloroform-like|Density = 0.8593 g cm−3 (at 20 Â°C)|MeltingPtC = −105

1152|11}}|BoilingPtC = 42|BoilingPt_ref =

reason=33% of what? And define "%"! Is it a mass fraction, volume fraction or mole fraction? We cannot read your mind, sorry!|date=May 2023}}|VaporPressure = 330 mmHg (20 Â°C)|MagSus = −47.3·10−6 cm3/mol}}|Section7={{Chembox Hazards|GHSPictograms = {{GHS02}}{{GHS07}}|GHSSignalWord = Danger

225

319|335}}

210

240

242

261

271

302+352

304+340

312

332+313

362

403+233

405|501}}|FlashPtC = −18

0396}}|ExploLimits = 2.2–13.8%|IDLH = 2200 ppm

109875|Methylal}}|LC50 = 18000 ppm (mouse, 7 hr)15000 ppm (rat)18354 ppm (mouse, 7 hr)|REL = TWA 1000 ppm (3100 mg/m3)}}|Section8={{Chembox Related|OtherFunction_label = Ethers|OtherFunction = Dimethoxyethane|OtherCompounds = }}}}Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and 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{{cln|reason=What on this Earth is "three parts water"? And define "part", because "part" is ambiguous on multiple levels! Is it a mass fraction, volume fraction or mole fraction? We cannot read your mind, sorry!|date=May 2023}} and miscible with most common organic solvents. Synthesis and structure 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.Due to the anomeric effect, dimethoxymethane has a preference toward the gauche conformation with respect to each of the C–O bonds, instead of the anti conformation. Since there are two C–O bonds, the most stable conformation is gauche-gauche, which is around 7 kcal/mol more stable than the anti-anti conformation, while the gauche-anti and anti-gauche are intermediate in energy.BOOK, Advanced organic chemistry, Carey, Francis A., Sundberg, Richard J., 2007, Springer, 9780387448978, 5th, New York, 154040953, 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. Applications 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. JOURNAL, 10.1016/j.combustflame.2020.04.016, A comprehensive kinetic model for dimethyl ether and dimethoxymethane oxidation and NO interaction utilizing experimental laminar flame speed measurements at elevated pressure and temperature, 2020, Shrestha, Krishna P., Eckart, Sven, Elbaz, Ayman M., Giri, Binod R., Fritsche, Chris, Seidel, Lars, Roberts, William L., Krause, Hartmut, Mauss, Fabian, Combustion and Flame, 218, 57–74, 10754/662921, free, Reagent in organic synthesis 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.BOOK, Wuts, P. G. M., Greene, T.W., 2006, Greene's Protective Groups in Organic Synthesis, 10.1002/0470053488, 9780470053485, J. Wiley, NY, This method is preferred to the use of chloromethyl methyl ether (MOMCl). Phenols can also be MOM-protected using dimethoxymethane, p-toluenesulfonic acid.JOURNAL, Yardley, John P., Fletcher, Horace, Introduction of the Methoxymethyl Ether Protecting Group, Synthesis, 1976, 1976, 04, 244–244, 10.1055/s-1976-24000, 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.JOURNAL, Synthesis of alpha-Halo Ethers from Symmetric Acetals and in situ Methoxymethylation of an Alcohol, Organic Syntheses, 2007, 84, 102, 10.15227/orgsyn.084.0102, Martin, Berliner, Katherine, Belecki., free, References {{Reflist}} External links {{PGCH|0396}} {{Authority control}}