109-87-5

Basic information

• Product Name: Dimethoxymethane
• Synonyms: DIMETHOXYMETHANE;DIMETHYLFORMAL;(CH3O)2CH2;2,4-Dioxapentane;Anesthenyl;bis(methoxy)methane;dimethoxy-methan;Dimethylacetal formaldehyde
• CAS NO: 109-87-5
• Molecular Formula: C₃H₈O₂
• Molecular Weight: 76.09
• EINECS: 203-714-2
• Product Categories: Organics
• Mol File: 109-87-5.mol
• Article Data: 229

Chemical Properties

• Melting Point: -105 °C
• Boiling Point: 41-43 °C
• Flash Point: -18 °C
• Appearance: Clear colorless/Liquid
• Density: 0.860 g/mL at 20 °C(lit.)
• Vapor Density: 2.6 (vs air)
• Vapor Pressure: 364.565mmHg at 25°C
• Refractive Index: n20/D 1.354
• Storage Temp.: 2-8°C
• Solubility: 32.3 g/100 mL (16°C)
• PKA: 3.1[at 20 ℃]
• Explosive Limit: 1.6-17.6%(V)
• Water Solubility: 32.3 g/100 mL (16 ºC)
• Sensitive: Moisture Sensitive
• Stability: Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point and wide explosive limits. Incompat
• Merck: 14,6012
• BRN: 1697025
• CAS DataBase Reference: Dimethoxymethane(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethoxymethane(109-87-5)
• EPA Substance Registry System: Dimethoxymethane(109-87-5)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-19-36-36/37/38
• Safety Statements: 16-26-33-7/9-37/39
• RIDADR: UN 1234 3/PG 2
• WGK Germany: 1
• RTECS: PA8750000
• F: 21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 109-87-5(Hazardous Substances Data)

Usage

Chemical Properties

Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It is stable in the presence of alkalis and mild acids, and to high temperatures and pressures. It differs from other ethers in that it forms only minute omounts of peroxides. It will dissolve such synthetic resins as nitrocellulose, cellulose acetate and propionate, ethyl cellulose, vinyl, "Epons" and polystyrene, and also many of the natural gums and waxes. Methylal as a latent solvent is activated by the addition of esters, ketones or alcohols. Its evaporation rate, twice that of acetone, places this ether in a class with such solvents as acetone, methyl acetate and ethyl acetate in resin formulations.

Physical properties

Dimethoxymethane appears as a clear colorless liquid with a pungent, chloroform-like odor. Flash point 0°F. Boiling point 42.3°C. Density 0.864 g / cm3 at 68°F (20°C). Vapors heavier than air.

Uses

Dimethoxymethane (Methylal) is a valuable extraction solvent for pharmaceutical products and a stable, inexpensive solvent for Grignard reactions. Methylal is stable under alkaline and mild acidic conditions. Its dissolving ability is stronger than ether, acetone, and methanol and azeotrope can dissolve nitrocellulose with high nitrogen content. Dimethoxymethane is mainly used in the production of anion-exchange resins, and also as solvents and special fuels.

Preparation

Dimethoxymethane synthesis is based on the liquid-phase acetalization reaction of methanol and formaldehyde. 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. Reaction mechanisms and catalysis in the one-step synthesis of methylal via methanol oxidationNovel Porous Iron Molybdate Catalysts for Synthesis of Dimethoxymethane from Methanol: Metal Organic Frameworks as Precursors

Application

Dimethoxymethane is a versatile chemical with applications in many industries such as paints, perfume, resins, pharmacy, paint strippers, protective coatings, and fuel additives.It may be used in the synthesis of methoxymethyl (MOM) ethers.It may also be used as an external cross-linker to form microporous polymers.Reaction solvent or an extraction solvent manufacturing pharmaceuticals, aerosols, paints, varnishes and cleanings.Production of ion exchange resins, polyacetal as a chain length regulator.Glue Formulations fragrances and pesticides.Fuel Additive for smoke reduction.Blowing agent for PU Foams.

Definition

ChEBI: Dimethoxymethane is an acetal that is the dimethyl acetal derivative of formaldehyde. It is an acetal and a diether. It derives from a methanediol.

General Description

Dimethoxymethane (DMM, methylal) is a biodegradable dimethyl acetal. It can be synthesized by acid catalyzed condensation of formaldehyde with methanol. It is amphiphilic in nature with low viscosity, surface tension and boiling point. It is a flammable, highly volatile solvent with good dissolving power. DMM is considered as a potential alternative fuel and fuel additive due to its high oxygen content and its ability to enhance the combustion characteristics of diesel and petrol. Its thermal diffusivity has been determined by photoacoustic method. Analysis of the molecular structure of DMM by electron diffraction technique shows that it has C2 symmetry with a gauche-gauche conformation.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

Dimethoxymethane, an acetal, is incompatible with strong oxidizing agents and acids . Breaks down to formaldehyde and methanol in acidic solutions. A very dangerous fire hazard when exposed to heat, flame or oxidizing agents. May ignite or explode if heated with oxygen [Lewis].

Health Hazard

VAPOR: Irritating to eyes, nose and throat. Harmful if inhaled. LIQUID: Irritating to skin and eyes. Harmful if swallowed.

Fire Hazard

FLAMMABLE. A very dangerous fire hazard when exposed to heat, flame, or oxidzers. Moderately explosive when exposed to heat or flame. May ignite or explode when heated with oxygen. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Flammability and Explosibility

Highlyflammable

Safety Profile

Moderately toxic by subcutaneous route. Mildly toxic by ingestion and inhalation. Can cause injury to lungs, liver, kidneys, and the heart. A narcotic and anesthetic in high concentrations.Dimethoxymethane is considered to be of low hazard potential to humans given that no adverse effects or organ-specific toxicity were observed at inhalation exposures as high as 10 068 ppm (31 334 mg/m3) in rats, and considering the available information indicating a lack of genotoxic, mutagenic or developmental effects. As dimethoxymethane is considered to be of low hazard potential, the risk to human health is considered to be low.

Potential Exposure

Vapors may form explosive mixture with air. Methylal may be able to form unstable and explosive peroxides. Heating may cause explosion. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Hydrolyzes readily in presence of acids to generate aldehydes.

Source

Methylal is a by-product in the synthesis of trioxane, an intermediate in the manufacture of polyacetal plastics (Albert et al., 2001).

Shipping

UN1234 Methylal, Hazard Class: 3; Labels: 3-Flammable liquid

Purification Methods

It is a volatile flammable liquid which is soluble in three parts of H2O, and is readily hydrolysed by acids. Purify it by shaking with an equal volume of 20% aqueous NaOH, stand for 20minutes, dry over fused CaCl2, filter and fractionally distil it through an efficient column. Store it over molecular sieves. [Buchler et al. Org Synth Coll Vol III 469 1955, Rambaud & Besserre Bull Soc Chim Fr 45 1955, IR: Wilmshurst Can J Chem 36 285 1958, Beilstein 1 IV 3026.]

Waste Disposal

Concentrated waste containing no peroxides: discharge liquid at a controlled rate near a pilot flame. Concentrated waste containing peroxides: perforation of containers of the waste from a safe distance followed by open burning.

InChI:InChI=1/C3H8O2/c1-4-3-5-2/h3H2,1-2H3

Synthetic route

methanol (67-56-1) + formaldehyd (50-00-0) → Dimethoxymethane (109-87-5) + Methyl formate (107-31-3)

Conditions	Yield
In water at 46 - 100℃; Acidic ion exchange resin;	A 98.2% B 0.6%
Katapak-catalyst In water at 46 - 100℃; Product distribution / selectivity;

methanol (67-56-1) + formaldehyd (50-00-0) → Dimethoxymethane (109-87-5)

Conditions	Yield
With sulfuric acid for 5h; Reagent/catalyst; Reflux;	96%
ion exchange resin with sulphonic acid groups In water at 70℃; for 0.2h; Industry scale;	95.9%
ion-exchange resines In water Product distribution; continuous apparatus (rectification of the formed methylal);

1-(methoxymethyl)-2-pyrrolidinone (22106-70-3) + chloromethyl methyl ether (107-30-2) → 1-(chloromethyl)pyrrolidin-2-one (31282-95-8) + Dimethoxymethane (109-87-5)

Conditions	Yield
Heating;	A 96% B n/a

dimethyldimethoxysilan (1112-39-6) + 2,2-dimethyl-[1,3,2]dioxasilinane (14879-83-5) → Dimethoxymethane (109-87-5) + 2,2,4,4,6-Pentamethyl-1,3-dioxa-2-silacyclohexane (77181-39-6)

Conditions	Yield
With tin(IV) chloride at 65℃; Product distribution; other reaction conditions; also with 1,3-dioxane and 4,4-dimethyl-1,3-dioxane;	A n/a B 94%

methanol (67-56-1) + phenylacetylene (536-74-3) → benzoic acid methyl ester (93-58-3) + Dimethoxymethane (109-87-5)

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene at 60℃; for 15h; Time; Reagent/catalyst; Concentration; Temperature; Sealed tube;	A 82% B n/a

Dimethyl ether (115-10-6) → methanol (67-56-1) + formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) + Methyl formate (107-31-3)

Conditions	Yield
With nitrogen; oxygen at 239.84℃; Conversion of starting material;	A 19.4% B 79% C 0.1% D 1.6%
With nitrogen; oxygen at 199.84 - 259.84℃; Rate constant;	A 17.3% B 69.2% C 0% D 1.6%
With nitrogen; oxygen at 239.84℃; Conversion of starting material;	A 22.4% B 60.1% C 0% D 5%

methanol (67-56-1) + dichloromethane (75-09-2) + carbon monoxide (201230-82-2) → Dimethoxymethane (109-87-5) + acetic acid methyl ester (79-20-9) + methyl methoxyacetate (6290-49-9) + malonic acid dimethyl ester (108-59-8)

Conditions	Yield
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; electrolysis;	A 8% B n/a C 3% D 74.5%
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; Product distribution; Mechanism; electrolysis, var. of catalyst, its reduction method, ratio;	A 8% B n/a C 3% D 74.5%
With sodium hydroxide; carbon-doped cobalt at 80℃; under 23560 Torr; for 1h;	A 1.2 % Chromat. B 7.5 % Chromat. C 1.9 % Chromat. D 28.8 % Chromat.

methanethiosulfonic acid S-methyl ester (2949-92-0) → formic acid (64-18-6) + methanesulfonic acid (75-75-2) + Dimethoxymethane (109-87-5) + Methyl formate (107-31-3)

Conditions	Yield
With oxygen In methanol Irradiation;	A n/a B 72% C n/a D n/a

4-octyl-1,3-dioxane (23433-02-5) → Dimethoxymethane (109-87-5) + undecane-1,3-diol (6071-32-5)

Conditions	Yield
With methanol; sulfuric acid Heating;	A n/a B 70%

methanol (67-56-1) + 1,2-dibromomethane (74-95-3) → Dimethoxymethane (109-87-5)

Conditions	Yield
With 4-vinylpyridine at 125℃; under 6000.6 Torr; for 2h;	58%

methanol (67-56-1) → Dimethoxymethane (109-87-5)

Conditions	Yield
With oxygen at 139.84℃; under 760.051 Torr; Reagent/catalyst; Temperature; Time; Inert atmosphere;	50%
With V(V) complex at 140℃; under 760.051 Torr; for 4h; Catalytic behavior; Temperature; Sealed tube; chemoselective reaction;	9%
With oxygen; Mo12V3W1.2Cu1.2Sb0.5Ox at 200 - 350℃; Product distribution / selectivity; Gas phase;	1.6%

methanol (67-56-1) + Methyl formate (107-31-3) → Dimethoxymethane (109-87-5)

Conditions	Yield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 80℃; under 60006 Torr; for 22h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Autoclave;	41%

methanol (67-56-1) + chloroprene (126-99-8) → Dimethoxymethane (109-87-5) + 2-chloro-3,3-dimethoxyprop-1-ene (16906-18-6) + methoxymethanol (4461-52-3) + acrylic acid methyl ester (292638-85-8)

Conditions	Yield
With ozone at -78℃; Further byproducts given;	A 24 % Spectr. B 40% C 75 % Spectr. D n/a

trans-4-tert-butylcyclohexanol (21862-63-5) + chloromethyl methyl ether (107-30-2) → Dimethoxymethane (109-87-5) + bis(4-tert-butylcyclohexyloxy)methane + trans-4-tert-butyl-O-(methoxymethyl)cyclohexanol (89726-87-4)

Conditions	Yield
Stage #1: chloromethyl methyl ether With 1H-imidazole In d7-N,N-dimethylformamide for 0.166667h; Stage #2: trans-4-tert-butylcyclohexanol for 24h;	A n/a B n/a C 40%

methanol (67-56-1) + 2-chloro-3-methylbutadiene (1809-02-5) → Dimethoxymethane (109-87-5) + acetic acid methyl ester (79-20-9) + methacrylic acid methyl ester (80-62-6) + 2-Chlor-3,3-dimethoxy-1-buten (108365-85-1)

Conditions	Yield
With ozone at -78℃; Further byproducts given. Yields of byproduct given;	A n/a B n/a C n/a D 39%

methanol (67-56-1) → Dimethoxymethane (109-87-5) + Methyl formate (107-31-3)

Conditions	Yield
With PHTHALIMAX S4 vanadia-titania catalyst; oxygen at 139.84℃; under 760.051 Torr; Inert atmosphere;	A 38% B n/a
at 150℃; for 18h; Product distribution;	A 0.72 mmol B 2.24 mmol
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 20℃; Product distribution; Further Variations:; Catalysts; Electrolysis;

methanol (67-56-1) → formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) + Dimethyl ether (115-10-6)

Conditions	Yield
With oxygen at 169.84℃; under 760.051 Torr; Inert atmosphere;	A n/a B 30% C n/a
With titanium(IV) oxide at 275℃;	A 49 %Chromat. B 7 %Chromat. C 44 %Chromat.
With oxygen at 249.84℃; for 1.16667h; chemoselective reaction;

methanol (67-56-1) → formaldehyd (50-00-0) + Dimethoxymethane (109-87-5)

Conditions	Yield
With oxygen at 159.84℃; under 760.051 Torr; Temperature; Inert atmosphere;	A n/a B 28%
With oxygen; iron(II) molybdate at 200 - 250℃; Product distribution / selectivity; Gas phase;	A n/a B 1.4%
molecular sieve at 230℃; Product distribution; Mechanism; other alcohols; other catalysts;

methanol (67-56-1) → Dimethoxymethane (109-87-5) + Dimethyl ether (115-10-6)

Conditions	Yield
With oxygen at 169.84℃; under 760.051 Torr; Reagent/catalyst; Temperature; Inert atmosphere;	A 28% B n/a
With oxygen; molybdenum(VI) oxide at 215℃; Product distribution; Investigation of methanol conversion in contact with MoO3 in a flow reactor in helium as a carrier gas. Investigation of the effect of the oxygen partial pressure in the reactive gas and reaction time in the absence of oxygen.;
With 2,6-di-tert-butyl-pyridine; H5PV2Mo10O40; oxygen; silica gel at 179.85℃; Product distribution; Further Variations:; Reagents;

methanol (67-56-1) → Dimethoxymethane (109-87-5) + Dimethyl ether (115-10-6) + Methyl formate (107-31-3)

Conditions	Yield
With oxygen at 159.84℃; under 760.051 Torr; Reagent/catalyst; Temperature; Inert atmosphere;	A 28% B n/a C n/a
With PHTHALIMAX S4 vanadia-titania catalyst; oxygen at 159.84℃; under 760.051 Torr; Inert atmosphere;	A 17% B n/a C n/a
With silicomolybdic acid at 170℃; for 1h; Product distribution; other reagents, other organic oxygen-containing compounds;

methanol (67-56-1) → Dimethoxymethane (109-87-5) + Methyl formate (107-31-3) + carbon dioxide (124-38-9)

Conditions	Yield
With phosphotungstic acid; platinum In water at 20℃; Product distribution; electrocatalytic oxidation of methanol investigated;	A n/a B 26% C n/a
With phosphotungstic acid; platinum In water at 20℃; electrocatalytic oxidation;	A n/a B 26% C n/a
With helium; water; oxygen at 24.9℃; under 757.6 Torr; Product distribution; gas phase fuel cell; variation of pressures;

1-hexadecene ozonide (81618-17-9) → Dimethoxymethane (109-87-5) + n-pentadecanal (2765-11-9) + Methyl formate (107-31-3) + palmitic acid (1002-84-2) + pentadecanoic acid methyl ester (7132-64-1) + 1,1-dimethoxy-pentadecane (52517-73-4)

Conditions	Yield
In methanol at 90℃; for 6h; Mechanism; Product distribution; Kinetics; other solvents; other objects of study: energy data, velocity constant;	A 19.6% B 8.8% C 21.3% D 20.3% E 2.2% F 14.1%

butyl-[1,2,4]trioxolane (767-09-9) + methanol (67-56-1) → pentanal (110-62-3) + Dimethoxymethane (109-87-5) + Methyl formate (107-31-3) + methyl valerate (624-24-8) + 1,1-dimethoxy-pentane (26450-58-8) + valeric acid (109-52-4)

Conditions	Yield
at 90℃; for 6h; Product distribution; Thermodynamic data; Rate constant; other temperature, ΔS (excit.), ΔG (excit.), ΔH (excit.);	A 2.8% B 18.3% C 20.4% D 3.7% E 18.4% F 15.9%

butyl-[1,2,4]trioxolane (767-09-9) → formaldehyd (50-00-0) + pentanal (110-62-3) + Dimethoxymethane (109-87-5) + Methyl formate (107-31-3) + 1,1-dimethoxy-pentane (26450-58-8) + valeric acid (109-52-4)

Conditions	Yield
In methanol at 90℃; for 6h; Mechanism; Product distribution;	A 2.1% B 2.8% C 18.3% D 20.4% E 18.4% F 15.9%

methanol (67-56-1) + dichloromethane (75-09-2) → Dimethoxymethane (109-87-5) + 1-((2R,4S,5R)-4-Ethoxymethoxy-5-ethoxymethoxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione (93298-60-3)

Conditions	Yield
With sodium hydroxide at 140℃;	A n/a B 19%

methanol (67-56-1) + di-n-butyloxymethane (2568-90-3) → Dimethoxymethane (109-87-5) + 1-butoxy-1-methoxymethane (76050-97-0) + butan-1-ol (71-36-3)

Conditions	Yield
at 160 - 180℃; reagiert analog mit Decylalkohol;

methanol (67-56-1) + formaldehyde-[bis-(2-methyl-butyl)-acetal] (412013-41-3) → Dimethoxymethane (109-87-5)

Conditions	Yield
With hydrogenchloride

methanol (67-56-1) + dichloromethane (75-09-2) → Dimethoxymethane (109-87-5)

Conditions	Yield
With sodium hydroxide at 100 - 125℃; unter Druck;
With sodium hydroxide at 100 - 125℃; unter Druck;

methanol (67-56-1) + bis(bromomethyl) ether (4497-29-4) → Dimethoxymethane (109-87-5)

methanol (67-56-1) + Chloromethyl acetate (625-56-9) → Dimethoxymethane (109-87-5) + acetic acid methyl ester (79-20-9)

Conditions	Yield
at 50℃;

Dimethoxymethane (109-87-5) + 2,2-Dimethyl-1,3-propanedithiol (53555-42-3) → 5,5-Dimethyl-1,3-dithiane (60311-39-9)

Conditions	Yield
With boron trifluoride diethyl etherate	100%
With boron trifluoride diethyl etherate; acetic acid In chloroform for 0.5h; Heating;	100%
	88.7%
With trifluoroborane diethyl ether; acetic acid In chloroform

Dimethoxymethane (109-87-5) + D,L-1,2,4-butanetriol (3068-00-6) → (1,3-dioxan-4-yl)methanol (4728-06-7)

Conditions	Yield
	100%

Dimethoxymethane (109-87-5) + 2,2-diethyl-1,3-propanedithiol (56472-17-4) → 5,5-Diethyl-1,3-dithiane (134434-07-4)

Conditions	Yield
With boron trifluoride diethyl etherate	100%
With boron trifluoride diethyl etherate; acetic acid In chloroform for 0.5h; Heating;	100%

Dimethoxymethane (109-87-5) + 2-(hydroxymethyl)butane-1,4-diol (6482-32-2) → 5-(2-hydroxyethyl)-1,3-dioxane (115430-92-7)

Conditions	Yield
	100%

Dimethoxymethane (109-87-5) + 3-Phenylpropenol (104-54-1) → γ-Phenyl-allylalkohol-methoxy-methylether (88738-40-3, 91970-13-7)

Conditions	Yield
With toluene-4-sulfonic acid; lithium bromide for 0.75h; Ambient temperature;	100%
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00555556h; Microwave irradiation;	98%
With 1-butyl-3-methylimidazolium tetrachloroindate for 0.025h; Microwave irradiation; chemoselective reaction;	97%
With tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate at 20℃; for 0.0833333h;	95%

Dimethoxymethane (109-87-5) + diethyl (2R,3R)-tartrate (87-91-2) → (+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate (100449-52-3)

Conditions	Yield
With phosphorus pentaoxide In chloroform for 2.5h; Ambient temperature;	100%
With phosphorus pentoxide In dichloromethane for 5h; Ambient temperature;	100%
With phosphorus pentoxide In chloroform for 2h; Alkylation;	97%
With phosphorus pentoxide In dichloromethane	96%
With phosphorus pentoxide In dichloromethane

Dimethoxymethane (109-87-5) + 1-Methylsulfanyl-4-phenyl-1-(toluene-4-sulfonyl)-butan-2-ol (107536-00-5) → 1-(2-Methoxymethoxy-1-methylsulfanyl-4-phenyl-butane-1-sulfonyl)-4-methyl-benzene (107536-02-7)

Conditions	Yield
With phosphorus pentoxide In chloroform for 1h; Ambient temperature;	100%

Dimethoxymethane (109-87-5) + 2-Methylsulfanyl-1-phenyl-2-(toluene-4-sulfonyl)-ethanol (107536-13-0) → 1-(2-Methoxymethoxy-1-methylsulfanyl-2-phenyl-ethanesulfonyl)-4-methyl-benzene (107536-05-0)

Conditions	Yield
With phosphorus pentoxide In chloroform for 1h; Ambient temperature;	100%

Dimethoxymethane (109-87-5) + 2β-bromo-1α,3β-dihydroxycycloheptane (74676-69-0) → 2β-bromo-1α,3β-bis(methoxymethoxy)-cycloheptane (74676-70-3)

Conditions	Yield
With phosphorus pentoxide In dichloromethane	100%

Dimethoxymethane (109-87-5) + L-(+)-diethyl tartrate (87-91-2, 13811-71-7, 21066-72-8, 57968-71-5, 122406-96-6, 128851-23-0) → 2,3-Bis-methoxymethoxy-succinic acid diethyl ester (100449-52-3)

Conditions	Yield
With phosphorus pentoxide	100%

Dimethoxymethane (109-87-5) + benzyl alcohol (100-51-6) → benzyl methoxymethyl ether (31600-55-2)

Conditions	Yield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide at 20℃; for 1h;	100%
zirconium(IV) chloride at 20℃; for 1h;	97%
With tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate at 20℃; for 0.0833333h;	97%

Dimethoxymethane (109-87-5) + diethyl (2R,3R)-tartrate (87-91-2) → trans-(4R,5R)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester (21154-13-2, 60077-28-3, 70561-17-0)

Conditions	Yield
With 3 A molecular sieve; Amberlyst 15 ion-exchange resin In ethyl acetate for 24h; Heating;	100%
With boron trifluoride diethyl etherate In Isopropyl acetate	100%

Dimethoxymethane (109-87-5) + 3-hydroxy-5-phenylisoxazole (939-05-9) → 2-Methoxymethyl-5-phenyl-isoxazol-3-one

Conditions	Yield
With phosphorus pentoxide In dichloromethane at 20℃; for 2h;	100%

Dimethoxymethane (109-87-5) + 3,3'-Dimethyl-biphenyl-2,2'-dithiol (190841-64-6) → 4,8-Dimethyl-5,7-dithia-dibenzo[a,c]cycloheptene

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane for 12h; Ambient temperature;	100%

Dimethoxymethane (109-87-5) + (1RS,2RS,3SR,4RS,5RS)-1-[(benzyloxy)methyl]-2-endo,4-endo-dibromo-8-oxabicyclo[3.2.1]oct-6-en-3-endo-ol → (1RS,2SR,3SR,4SR,5RS)-1-[(benzyloxy)methyl]-2-endo,4-endo-dibromo-3-(methoxymethoxy)-8-oxabicyclo[3.2.1]oct-6-ene

Conditions	Yield
With phosphorus pentoxide at 20℃; for 0.166667h;	100%
With phosphorus pentoxide In dichloromethane at 20℃;	89%

Dimethoxymethane (109-87-5) + diethyl (2S,3S)-tartrate (13811-71-7) → diethyl (2S,3S)-2,3-di-O-methoxymethyl-tartrate (159593-22-3)

Conditions	Yield
With phosphorus pentoxide In dichloromethane	100%
With phosphorus pentoxide In dichloromethane for 3h;	100%
With phosphorus pentoxide In chloroform for 2h; Alkylation;	84%
With phosphorus pentoxide In dichloromethane
With phosphorus pentoxide In dichloromethane at 0℃; for 10h; Inert atmosphere;

Dimethoxymethane (109-87-5) + (1R,4S,5S,6S)-6-Hydroxy-4,5-bis-methoxymethoxy-6-triisopropylsilanyloxymethyl-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester → (3aS,4R,7S,7aS)-7-Methoxymethoxy-3a-triisopropylsilanyloxymethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-4,5-dicarboxylic acid dimethyl ester

Conditions	Yield
With phosphorus pentoxide at 0℃; Condensation; Cyclization;	100%

Dimethoxymethane (109-87-5) + C28H25NO8 (347377-80-4) → C29H25NO8 (347377-82-6)

Conditions	Yield
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate at 0 - 20℃; for 12h;	100%

Dimethoxymethane (109-87-5) + methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate (122743-18-4) → (4R,5S)-5-Phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Conditions	Yield
With phosphorus pentoxide In dichloromethane for 1h;	100%

Dimethoxymethane (109-87-5) + (2R,3S)-2,3-Dihydroxy-butyric acid methyl ester (117406-91-4) → (4S,5R)-5-Methyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Conditions	Yield
With phosphorus pentoxide In dichloromethane for 1h;	100%

Dimethoxymethane (109-87-5) + (R)-2,3-dihydroxy-2-methyl-propionic acid methyl ester (147501-89-1) → (R)-4-Methyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Conditions	Yield
With phosphorus pentoxide In dichloromethane for 1h;	100%

Dimethoxymethane (109-87-5) + (2R,3S)-4-Benzyloxy-2,3-dihydroxy-butyric acid methyl ester (401479-91-2) → (4R,5S)-5-Benzyloxymethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Conditions	Yield
With phosphorus pentoxide In dichloromethane for 1h;	100%

Dimethoxymethane (109-87-5) + (-)-(2S)-5-benzenesulfonyl-1-tosyloxy-pent-3-ene-2-ol (435286-39-8) → (+)-(2S)-5-benzenesulfonyl-2-methoxymethoxy-1-tosyloxy-pent-3-ene (527729-31-3)

Conditions	Yield
With phosphorus pentoxide In chloroform at 20℃; for 1h;	100%

Dimethoxymethane (109-87-5) + (2S)-2-hydroxy-1,4-bis<(methansulfonyl)oxy>butane (5055-10-7) → (S)-1,4-di-O-mesyl-O-(methoxymethyl)-1,2,4-butanetriol (532983-45-2)

Conditions	Yield
With phosphorus pentoxide In chloroform at 20℃; for 0.75h;	100%

Dimethoxymethane (109-87-5) + para-Chlorobenzyl alcohol (873-76-7) → 1-chloro-4-[(methoxymethoxy)methyl]benzene (1200-16-4)

Conditions	Yield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide at 20℃; for 1.2h;	100%
With zirconyl triflate at 20℃; for 0.166667h; neat (no solvent); chemoselective reaction;	100%
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00555556h; Microwave irradiation;	98%

Dimethoxymethane (109-87-5) + Ergosterol (57-87-4) → O-methoxymethyl-ergosterol (95307-27-0)

Conditions	Yield
With phosphorus pentoxide	100%
With phosphorus pentoxide at 20℃; for 1h;	89%

Dimethoxymethane (109-87-5) + ethyl 4,7-dihydro-4β,7β-ethano-2H-isoindole-1-carboxylate (200353-88-4) → bis(3-ethoxycarbonyl-4,7-dihydro-4,7-ethano-2H-isoindol-1-yl)methane (663905-19-9)

Conditions	Yield
With sulfuric acid In dichloromethane; acetic acid at 20℃; for 1h;	100%

1-(3-bromo-4-hydroxyphenyl)-acetone (655237-87-9) + Dimethoxymethane (109-87-5) → 1-[3-bromo-4-(methoxymethoxy)phenyl]acetone (873804-36-5)

Conditions	Yield
With phosphorus pentoxide In toluene at -5 - 5℃; for 17h; Product distribution / selectivity;	100%

Dimethoxymethane (109-87-5) + 2,4,6-trihydroxyacetophenone (480-66-0) → 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone (65490-09-7)

Conditions	Yield
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide In dichloromethane at 20 - 30℃; for 3.5h; Stage #2: 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 10℃;	100%
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide at 20℃; for 2h; Inert atmosphere; Stage #2: 2,4,6-trihydroxyacetophenone With diisopropylamine In dichloromethane for 3h; Inert atmosphere; Cooling with ice; regioselective reaction;	50%
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide In dichloromethane at 20℃; for 3.5h; Stage #2: 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane at 5℃;

Dimethoxymethane (109-87-5) + (2,6-dibromo-3,5-dihydroxyphenyl)(3,5-dichloro-2-hydroxy-6-methoxy-4-methylphenyl)methanone (1258391-68-2) → (2,6-dibromo-3,5-bis(methoxymethoxy)phenyl)(3,5-dichloro-2-hydroxy-6-methoxy-4-methylphenyl)methanone (1258391-78-4)

Conditions	Yield
With phosphorus pentoxide at 20℃; for 3h;	100%

Upstream product

• 56-40-6 Glycine 
• 7722-84-1 Hydrogen peroxide 
• 30525-89-4 Paraformaldehyde 
• 67-56-1 Methanol 

Downstream Products

• 50-00-0 Formaldehyde 
• 160430-64-8 Acetamiprid 
• 772-33-8 2-HYDROXY-5-NITROBENZYL BROMIDE 
• 62013-04-1 Dirithromycin 
• 505-23-7 1,3-Dithiane 

Recommend Products

• 74498-88-7  β-Methoxyethyl-methyl-formal 
• 81216-08-2  1-(2-methoxy-ethoxy)-2-methoxymethoxy-ethane 
• 75-21-8  oxirane 
• 5732-48-9  1,2-bis-methoxymethoxy-ethane 
• 646-06-0  1,3-DIOXOLANE 
• 4341-34-8  2,2'-dithienylmethane 
• 188290-36-0  thiophene 
• 15937-81-2  1,3-bis(2-pyridyl)propane 
• 109-06-8  α-picoline 
• 13093-19-1  N,N'-Methylen-di-ε-caprolactam 
• 105-60-2  caprolactam 
• 26278-67-1  1,3-dimethoxy-1-phenylpropane 
• 100-42-5  styrene 
• 13353-03-2  bis-methoxymethoxy-methane 

Related news

ArticleOne-step aldol condensation reaction of Dimethoxymethane (cas 109-87-5) and methyl acetate over supported Cs/ZSM-35 zeolite catalysts08/28/2019

This study was performed for the development of a green and promising approach for the synthesis of methyl acrylate and acrylic acid by a one-step aldol condensation reaction of dimethoxymethane and methyl acetate over cesium oxide-supported on ZSM-35 zeolite catalysts; the effect of base sites ...detailed

Research paperReaction of Dimethoxymethane (cas 109-87-5) with hydroxyl radicals: An experimental kinetic study at temperatures above 296 K and pressures of 2, 5, and 10 bar08/27/2019

The rate coefficient of the reaction of dimethoxymethane with OH radicals was determined in a slow-flow reactor with pulsed laser photolysis/laser-induced fluorescence technique. Temperatures ranged from 297 to 570 K at nominal pressures of 2, 5, and 10 bar (bath gas: helium). The very weak temp...detailed

Full Length ArticleThermal stability and safety of Dimethoxymethane (cas 109-87-5) oxidation at low temperature08/26/2019

In this work, thermal oxidation reaction of dimethoxymethane (DMM) at low temperature was investigated with a custom-designed mini closed pressure vessel test (MCPVT) employed. The initial auto-oxidation, thermal decomposition and deep radical oxidation processes were revealed by analyzing the b...detailed

Full Length ArticleCapturing methanol and Dimethoxymethane (cas 109-87-5) gases with ionic liquids08/24/2019

In this work, ionic liquid (IL) as green solvent was first proposed for capturing methanol and dimethoxymethane (DMM) gases released in the fuel synthesis process. The hydrophilic IL [EMIM][BF4] was selected from 192 kinds of ILs by the COSMO-RS model. The separation mechanism was revealed at th...detailed

Research articleGas and soot formed in the Dimethoxymethane (cas 109-87-5) pyrolysis. Soot characterization08/21/2019

The many simultaneous processes occurring within in a diesel engine make difficult a thorough understanding of the mechanisms responsible for reduction of soot and/or NOX when an oxygenated compound is added to diesel fuel. Thus, in order to explore the use of oxygenated compounds as biofuels/ad...detailed

Pyrolysis of Dimethoxymethane (cas 109-87-5) and the reaction of Dimethoxymethane (cas 109-87-5) with H atoms: A shock-tube/ARAS/TOF-MS and modeling study08/20/2019

Dimethoxymethane (CH3OCH2OCH3, DMM) is the smallest oxymethylene ether and currently discussed as a promising alternative diesel fuel. For an adequate modeling of the DMM combustion chemistry, reliable kinetic parameters are needed. In the present work, shock-tube studies are presented on the ki...detailed