4431-83-8

Basic information

• Product Name: BIS(2-METHOXYETHOXY)METHANE
• Synonyms: BIS(2-METHOXYETHOXY)METHANE;Formaldehyde 2-methoxyethyl acetal~2,5,7,10-Tetraoxaundecane;2,5,7,10-tetraoxaundecane;Formaldehyde2-methoxyethylacetal;Formaldehyde bis(2-methoxyethyl)acetal;1-methoxy-2-(2-methoxyethoxymethoxy)ethane;bis-(2-methoxy-aethoxy)-methan
• CAS NO: 4431-83-8
• Molecular Formula: C₇H₁₆O₄
• Molecular Weight: 164.2
• EINECS: 224-631-8
• Product Categories: blocks;BuildingBlocks
• Mol File: 4431-83-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 60°C 1,5mm
• Flash Point: 60°C/1.5mm
• Appearance: /
• Density: 0,995 g/cm3
• Vapor Pressure: 1.17mmHg at 25°C
• Refractive Index: 1.4140
• Water Solubility: Fully miscible in water.
• BRN: 1700087
• CAS DataBase Reference: BIS(2-METHOXYETHOXY)METHANE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(2-METHOXYETHOXY)METHANE(4431-83-8)
• EPA Substance Registry System: BIS(2-METHOXYETHOXY)METHANE(4431-83-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 4431-83-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4431-83-8 differently. You can refer to the following data:
1. bis(2-Methoxyethoxy)methane is a useful research chemical.
2. bis(2-Methoxyethoxy)methane is used in preparation of tetraoxaundecane by aldol condensation of ethylene glycol monomethyl ether and formaldehyde.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2748, 1989 DOI: 10.1021/jo00272a055

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H16O4/c1-8-3-5-10-7-11-6-4-9-2/h3-7H2,1-2H3

Synthetic route

formaldehyd (50-00-0) + 2-methoxy-ethanol (109-86-4) → bis(dimethoxyethyoxyl)methane (4431-83-8)

Conditions	Yield
With Amberlyst15 catalyst In water; toluene Reagent/catalyst; Solvent; Reflux;	94.4%
With iron(III) chloride bei langsamer Destillation;
With toluene-4-sulfonic acid In benzene Heating;
With toluene-4-sulfonic acid In toluene
With sulfuric acid beim Kochen;

diiodomethane (75-11-6) + 2-methoxy-ethanol (109-86-4) → bis(dimethoxyethyoxyl)methane (4431-83-8)

Conditions	Yield
tetrabutylammomium bromide In benzene at 75℃; for 5h; Product distribution; effect of temperature, various catalysts, various dihalomethanes, further alcohols;	58%

2-methoxy-ethanol (109-86-4) + 2-Methoxyethoxymethyl chloride (3970-21-6) → bis(dimethoxyethyoxyl)methane (4431-83-8)

Conditions	Yield
for 4h; Ambient temperature;

(2S,3S)-2,3-Bis(2-methoxyethoxymethoxy)-1,4-bis(4'-methylphenylsulfonyloxy)butane (216440-54-9) → bis(dimethoxyethyoxyl)methane (4431-83-8) + (4R,5R)-4,5-Bis-iodomethyl-[1,3]dioxolane

Conditions	Yield
With sodium iodide 1.) acetone, reflux, overnight, 2.) 110 deg C, 0.05 mmHg; Multistep reaction. Title compound not separated from byproducts;

formaldehyd (50-00-0) + 2-methoxy-ethanol (109-86-4) + sulfuric acid (7664-93-9) → bis(dimethoxyethyoxyl)methane (4431-83-8)

thionyl chloride (7719-09-7) + bis(dimethoxyethyoxyl)methane (4431-83-8) → 2-Methoxyethoxymethyl chloride (3970-21-6)

Conditions	Yield
With sulfur dioxide	70%

bis(dimethoxyethyoxyl)methane (4431-83-8) + chlorodiphenylphosphonium tetrachloroaluminate → <(2-methyoxyethoxy)methyl>diphenylphosphine oxide

Conditions	Yield
In diethyl ether for 1.5h; Heating;	61%

bis(dimethoxyethyoxyl)methane (4431-83-8) + glycolonitrile (107-16-4) → [(2-methoxy-ethoxy)-methoxy]-acetonitrile

Conditions	Yield
With sulfuric acid
With sulfuric acid

bis(dimethoxyethyoxyl)methane (4431-83-8) → 2-(2-methoxy-ethoxymethoxy)-ethanol (41633-60-7)

Conditions	Yield
With sulfuric acid; sodium carbonate In ethylene glycol

homoalylic alcohol (627-27-0) + bis(dimethoxyethyoxyl)methane (4431-83-8) → 4-chlorotetrahydro-2H-pyran (1768-64-5)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0℃; for 1h;	97 % Chromat.

homoalylic alcohol (627-27-0) + bis(dimethoxyethyoxyl)methane (4431-83-8) → (2S,4S)-4-Chloro-2-methyl-tetrahydro-pyran (92826-98-7)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 22℃; for 3h;	93 % Chromat.

bis(dimethoxyethyoxyl)methane (4431-83-8) + (E)-3-hexen-1-ol (928-97-2) → trans-3-ethyl-4-chlorotetrahydropyran (25999-33-1) + cis-3-ethyl-4-chlorotetrahydropyran (25999-40-0)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Upstream product

• 50-00-0 formaldehyd 
• 109-86-4 2-methoxy-ethanol 
• 3970-21-6 2-Methoxyethoxymethyl chloride 
• 7664-93-9 sulfuric acid 
• 216440-54-9 (2S,3S)-2,3-Bis(2-methoxyethoxymethoxy)-1,4-bis(4'-methylphenylsulfonyloxy)butane 
• 75-11-6 diiodomethane 

Downstream Products

• 3970-21-6 2-Methoxyethoxymethyl chloride 
• 1768-64-5 4-chlorotetrahydro-2H-pyran 

Relevant articles and documents

Preparation method of bis(dimethoxyethoxy)methane

Relating to the technical field of chemical synthesis, the invention discloses a preparation method of bis(dimethoxyethoxy)methane. The method includes the steps of: subjecting ethylene glycol monomethyl ether and formaldehyde to aldol condensation reaction under the action of an acid catalyst to prepare bis(dimethoxyethoxy)methane; wherein the molar ratio of formaldehyde to ethylene glycol monomethyl ether is 1:2-4; the dosage of the acid catalyst is 0.1-10%; the reaction temperature is 60-140DEG C, and the reaction time is 0.5-24h. The method provided by the invention utilizes acid to catalyze the reaction of ethylene glycol monomethyl ether and formaldehyde to generate bis(dimethoxyethoxy)methane, and belongs to economical reaction, the product includes water and is free of byproduct, and the catalyst has small corrosion to equipment, therefore the method is a clean bis(dimethoxyethoxy)methane synthesis method capable of recycling the catalyst, and is suitable for industrial continuous production.

Preparation of Cyclic Ethers via a Transacetalization-Cationic Cyclization Sequence

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Formals.

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