111-77-3

Basic information

• Product Name: 2-(2-Methoxyethoxy)ethanol
• Synonyms: METHYLDIETHYLENEGLYCOL;Diethylenglycolmonomethylether;Methoxyethoxy)ethanol, 2-(2-: (Diethylene glycol monomethyl ether);2-(2-methoxyethoxy)ethanol diethylene glycol monomethyl ether;2-(2-Methoxyethoxy)ethanol, Methyldiglycol;2-(2-Methoxyethoxy)ethanol, DOWANOL(R) DM, Methyldiglycol;2-(2-Methoxyethoxy)ethanol,99%;2-(2-Methoxyethoxy)e
• CAS NO: 111-77-3
• Molecular Formula: C₅H₁₂O₃
• Molecular Weight: 120.15
• EINECS: 203-906-6
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols;Organics;Quinolines
• Mol File: 111-77-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: −70 °C(lit.)
• Boiling Point: 194 °C(lit.)
• Flash Point: 183 °F
• Appearance: Clear/Liquid
• Density: 1.023 g/mL at 25 °C(lit.)
• Vapor Density: 4.14 (vs air)
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.426
• Storage Temp.: Store below +30°C.
• PKA: 14.37±0.10(Predicted)
• Explosive Limit: 1.38-22.7%
• Water Solubility: Miscible
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents. Hygroscopic. Store under nitrogen.
• Merck: 14,6037
• BRN: 1697812
• CAS DataBase Reference: 2-(2-Methoxyethoxy)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Methoxyethoxy)ethanol(111-77-3)
• EPA Substance Registry System: 2-(2-Methoxyethoxy)ethanol(111-77-3)

Safety Data

• Hazard Codes: Xn
• Statements: 63
• Safety Statements: 36/37
• WGK Germany: 1
• RTECS: KL6125000
• TSCA: Yes
• Hazardous Substances Data: 111-77-3(Hazardous Substances Data)

Usage

Chemical Properties

Diethylene glycol monomethyl ether (DEGME) is a type of glycol ether and is a colorless, stable hygroscopic liquid with an agreeable odor. It is completely miscible with water, ketones, alcohol, ethers, aromatic hydrocarbons and halogenated hydrocarbons. More specifically, it is miscible with acetone, benzene, carbon tetrachloride, ethyl ether, methanol and water. Exposure to diEGBE is unlikely to occur via inhalation unless it is heated. Diethylene glycol monomethyl ether is a solvent for dyes, oils, fats, waxes, many natural and synthetic resins, nitrocellulose and cellulose acetate. It is used as a high-boiling solvent in such formulations as printing inks ond pastes, stamp pad inks, textile dye pastes, lacquers, and synthetic resin coatings. Its presence in lacquers eases brushability and flow-out, and minimizes lifting of undercoats. DEGME is an ethylene-series or E-series glycol ether and is sold by Dow under the tradename Methyl CARBITOL? solvent. DEGME has a high dilution ratio and a low evaporation rate.It is stable under recommended storage conditions and readily biodegradable.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Different sources of media describe the Uses of 111-77-3 differently. You can refer to the following data:
1. Diethylene glycol monomethyl ether(DGME) is used as a thermally stable solvent for many substances, such as nitrocellulose, lacquers, varnishes, and dyes.
2. Diethylene glycol monomethyl ether is an industrial solvent and is also commonly used as a Fuel System Icing Inhibitor (FSII) in jet fuels.
3. Diethylene glycol monomethyl ether is used in textile dye pastes, in lacquer industrial for thinners and quick drying varnishes; solvent for wood stains, hydraulic brake fluid diluent, and as a coupling agent for miscible organic aqueous systems. Diethylene glycol monoethyl ether is used as a solvent in lacquer, varnishes, and enamels. It is also used in cosmetic products and dermatological preparations and as a solvent in some medicine products. It enhances the percutaneous absorption through the skin and mucosal barriers. It is used in some drugs to enhance absorption. Diethylene glycol monobutyl ether is used as a solvent in paints, dyes, inks detergents, and cleaners. Used in the same way as 2-ethoxyethanol where a solvent with a higher boiling point is required.

Definition

ChEBI: A hydroxypolyether that is the monomethyl ether derivative of diethylene glycol.

Preparation

A by-product in the manufacture of ethylene glycol monomethyl ether (Arctander, 1969).

General Description

Colorless liquid with a sweet odor. Floats and mixes with water.

Air & Water Reactions

Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154, 164]. Water soluble.

Reactivity Profile

2-(2-Methoxyethoxy)ethanol is a ether-alcohol derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Health Hazard

DGME is a mild to moderate toxicant via ingestion or absorption through the skin. High doses produced lowering of hemoglobin levels and increased relative kidney weight. Renaldamagemay occurnear the lethal dose. Eye contact of the liquid can result in mild to moderate irritationLD50 value, oral (guinea pigs): 4160 mg/kgPreliminary developmental toxicity test in pregnant mice dosed with DGME indicated teratogenicity of this compound (Hardin et al. 1987; Cheever et al. 1988). Earlier, Doe (1984) reported no teratogenic property of DGME when administered subcutaneously in rats up to 100 mL/kg. In comparison, EGME produced effects at 40 mL/kg..

Fire Hazard

2-(2-Methoxyethoxy)ethanol is combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by skin contact and intraperitoneal routes. Mildly toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. An eye irritant. Combustible when exposed to heat or flame; can react with oxidzing materials. Reacts violently with Ca(OCl)2, chlorosulfonic acid, and oleum. To fight fire, use dry chemical, alcohol foam, water spray or mist, CO2. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

Purification Methods

Purify as for diethylene glycol mono-n-butyl ether. [Beilstein 1 IV 2392.]

Waste Disposal

DGME is mixed with a combustible solvent and burned in a chemical incinerator.

InChI:InChI=1/C5H12O3/c1-5(7)4-8-3-2-6/h5-7H,2-4H2,1H3

Synthetic route

4-hydroxybenzyl 2-(2-methoxyethoxy)ethyl ether (115319-74-9) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
With iron(III) chloride Product distribution / selectivity;	97%

triethylene glucol monomethyl ether (112-35-6) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + diethylene glycol dimethyl ether (111-96-6)

Conditions	Yield
nickel; rhodium; palladium at 220℃; Product distribution / selectivity;	A 10% B 68%
5%-palladium/activated carbon; nickel at 220℃; Product distribution / selectivity;	A 5% B 67%
rhenium; nickel; palladium at 220℃; Product distribution / selectivity;	A 16% B 63%

ethyl 2-(1-(1-imidazolylcarbonyloxy)-2-methylpropyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (222634-34-6) → ethyl 2-(1-(2-(2-methoxyethoxy) ethoxycarbonyloxy)-2-methylpropyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (222634-37-9) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
	A 52% B n/a

oxirane (75-21-8) + methanol (67-56-1) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
unter Druck;
With potassium hydroxide unter Druck;
unter Druck;
With potassium hydroxide unter Druck;

(2-methoxy-ethyl)-(2-sulfooxy-ethyl)-ether → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
With sulfuric acid at 32.5℃; Equilibrium constant;

α-naphthol (90-15-3) + OO-tert-butyl methoxyethoxyethyl monoperoxycarbonate (67834-62-2) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 2-tert-Butoxy-naphthalen-1-ol + Carbonic acid 1-hydroxy-naphthalen-2-yl ester 2-(2-methoxy-ethoxy)-ethyl ester + tert-butyl alcohol (75-65-0)

Conditions	Yield
In various solvent(s) at 120℃; for 6h; Further byproducts given;

toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester (50586-80-6) → 1,4-dioxane (123-91-1) + methanol (67-56-1) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
With ethanol; thiourea at 85℃; Rate constant; Mechanism; other 1,1-d2 substituted tosylates; other reagents, var. temp.;

C23H32O6 (81194-70-9) → benzophenone (119-61-9) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 30℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), var. temp.;

OO-tert-butyl methoxyethoxyethyl monoperoxycarbonate (67834-62-2) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + methane (34557-54-5) + dicumene (1889-67-4) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
With Isopropylbenzene at 130℃; for 42h; Product distribution; Kinetics; Rate constant; other temperature; other solvent; other time; in the presence of styrene; E(excit.);	A 1.98 g B 0.07 g C 1.95 g D 0.24 g E 2.24 g

bis(methoxyethoxyethyl) peroxydicarbonate (40835-42-5) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + diethylene glycol dimethyl ether (111-96-6) + carbon dioxide (124-38-9) + Glycolaldehyde (141-46-8) + Carbonic acid 2-hydroxy-1-(2-methoxy-ethoxy)-ethyl ester 2-(2-methoxy-ethoxy)-ethyl ester

Conditions	Yield
In benzene at 60℃; Rate constant; Kinetics; Mechanism; var. temp., also with inhibiting addition of styrene or α-naphthol, Eact; other peroxydicarbonates;

ethylidene-bis- → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + diethylene glycol ethyl methyl ether (1002-67-1)

Conditions	Yield
With nickel at 170 - 210℃; Hydrogenation.unter Druck;

1,1-bis-[2-(2-methoxy-ethoxy)-ethoxy]-ethane (66854-10-2) + Raney nickel → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + diethylene glycol ethyl methyl ether (1002-67-1)

Conditions	Yield
at 170 - 210℃; under 51485.6 Torr; Hydrogenation;

oxirane (75-21-8) + methanol (67-56-1) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 2-methoxy-ethanol;O-methyl-triethylene glycol

Conditions	Yield
With sodium methylate

α-naphthol (90-15-3) + OO-tert-butyl methoxyethoxyethyl monoperoxycarbonate (67834-62-2) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + methane (34557-54-5) + 2-tert-Butoxy-naphthalen-1-ol + acetone (67-64-1) + Carbonic acid 1-hydroxy-naphthalen-2-yl ester 2-(2-methoxy-ethoxy)-ethyl ester + tert-butyl alcohol (75-65-0) + CO2, bicumyl

Conditions	Yield
In various solvent(s) at 120℃; for 6h; Rate constant; Product distribution; decomposition with variation of additives and solvents;

...Expand

3-<2-(2-Methoxyethoxy)ethoxy>propen (13752-97-1) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
With samarium diiodide; water; isopropylamine In tetrahydrofuran at 20℃; for 0.0166667h;

methanol (67-56-1) + diethylene glycol (111-46-6) → 1,4-dioxane (123-91-1) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + diethylene glycol dimethyl ether (111-96-6)

Conditions	Yield
With NAFION 1100 EW Polymer (H+ form) at 198 - 200℃; under 41890.1 Torr; for 5h;

diethylene glycol dimethyl ether (111-96-6) → methanol (67-56-1) + formaldehyd (50-00-0) + 1,2-dimethoxyethane (110-71-4) + methoxyethene (107-25-5) + 1-methoxy-2-ethoxyethane (5137-45-1) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + methane (34557-54-5) + Dimethyl ether (115-10-6) + ethyl methyl ether (540-67-0) + 2-methoxy-ethanol (109-86-4) + 2-methoxyethyl vinyl ether (1663-35-0)

Conditions	Yield
at 163℃; Irradiation; Inert atmosphere;

...Expand

2-methoxy-ethanol (109-86-4) + 2-chloro-ethanol (107-07-3) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
Stage #1: 2-methoxy-ethanol With sodium hydride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere; Cooling with ice; Stage #2: 2-chloro-ethanol In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Cooling with ice;	3.12 g

diethylene glycol dimethyl ether (111-96-6) → 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
With hydrogenchloride at 60 - 80℃;

C6H12O4 → formic acid (64-18-6) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3)

Conditions	Yield
With water at 80℃; for 24h; Equilibrium constant; Sealed tube;

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + methanesulfonyl chloride (124-63-0) → methanesulfonic acid 2-(2-methoxyethoxy)ethyl ester (60696-83-5)

Conditions	Yield
With triethylamine In diethyl ether for 0.5h;	100%
With triethylamine In diethyl ether	97%
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice;	94%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester (50586-80-6)

Conditions	Yield
With pyridine at 0 - 20℃; for 2h;	100%
Stage #1: 2-(2-methoxyethoxy)ethyl alcohol; p-toluenesulfonyl chloride With dmap In dichloromethane at 20℃; Stage #2: With triethylamine In dichloromethane at 20℃;	100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; Cooling with ice;	99%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 3,3,7,7-tetramethyl-2,8-dioxa-5-aza-1λ3-phosphabicyclo(3,3,0)octane (75194-94-4) → 8-[2-(2-methoxy-ethoxy)-ethoxy]-2,2,6,6-tetramethyl-tetrahydro-8λ5-[1,3,2]oxazaphospholo[2,3-b][1,3,2]oxazaphosphole

Conditions	Yield
In acetonitrile Addition;	100%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → C10H23O7P

Conditions	Yield
With pyridine; phosphorus trichloride In diethyl ether at 20℃; for 16h; Cooling with ice;	100%
With phosphorus trichloride In benzene for 2h; Heating;	80%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 7-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (193002-25-4) → 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (199328-77-3)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 0 - 20℃; for 1.5h;	100%

N-Ethylimidazole (7098-07-9) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + dimethyl sulfate (77-78-1) → 1-ethyl-3-methylimidazolium diethyleneglycolmonomethylether sulfate

Conditions	Yield
Stage #1: N-Ethylimidazole; dimethyl sulfate at 0 - 20℃; Stage #2: 2-(2-methoxyethoxy)ethyl alcohol at 160℃; for 5h;	100%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 5-Hydroxyisophthalic acid (618-83-7) → C18H26O9

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 72h; Reflux; Dean-Stark;	100%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + L-N-Boc-Ala (15761-38-3) → 2-(2-methoxyethoxy)ethyl (2S)-2-(tert-butoxycarbonylamino)propanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; Inert atmosphere;	100%

N-(tert-butoxy)-L-alanine + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 2-(2-methoxyethoxy)ethyl (2S)-2-(tert-butoxycarbonylamino)propanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 20℃; Inert atmosphere;	100%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + p-toluenesulfonyl chloride (98-59-9) → 2-methoxy-ethyl p-toluenesulfonyloxy ester (17178-10-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	100%

methylene chloride (74-87-3) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 1,2-dimethoxyethane (110-71-4)

Conditions	Yield
With sodium hydroxide In water at 60℃;	99.8%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + p-toluenesulfonyl chloride (98-59-9) → 2-<2-<2-<2-(benzyloxy)ethoxy>ethoxy>ethoxy>ethyl 4-methylbenzenesulfonate (89346-82-7)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 15h; Cooling with ice;	99.6%

phosgene (75-44-5) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 2-(2-methoxyethoxy)ethyl carbonochloridate (50689-80-0)

Conditions	Yield
at 3 - 5℃; for 3h;	99%
In toluene at 20℃; for 4h;
In benzene
In toluene at 0 - 20℃; Inert atmosphere;

3,5-bis(prop-2-yn-1-yloxy) benzoic acid (664334-21-8) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → C18H20O6

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 24h;	99%

2-(4-methoxybenzyloxy)-4-methylquinoline (937184-70-8) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + methyl trifluoromethanesulfonate (333-27-7) → C13H20O4 + 1,4-dimethylquinolin-2(1H)-one (2584-47-6) + 4,4'-dimethoxydibenzyl ether (5405-95-8)

Conditions	Yield
With magnesium oxide In various solvent(s) at 0 - 20℃;	A 98% B n/a C n/a

2-benzyloxy-1-methylpyridinium triflate + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → diethylene glycol benzyl methyl diether

Conditions	Yield
In α,α,α-trifluorotoluene at 120℃; for 0.333333h; Microwave irradiation;	98%
With magnesium oxide In α,α,α-trifluorotoluene at 80℃; for 24h;	93%
With magnesium oxide In α,α,α-trifluorotoluene at 83℃; for 24h;	93%
With magnesium oxide at 83℃; for 24h; Inert atmosphere;	93%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 2,4,6-tris(benzyloxy)-1,3,5-triazine (7285-83-8) → diethylene glycol benzyl methyl diether

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 2.66667h; Molecular sieve; Inert atmosphere;	98%
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 5h; Inert atmosphere;	95%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + p-toluenesulfonyl chloride (98-59-9) → 2-(2-methoxyethoxy)ethyl-4-methylbenzenesulfonate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h;	98%

maleic anhydride (108-31-6) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → (3-diethylene glycol monomethyl ether carbonyl)acrylic acid

Conditions	Yield
With triethylamine In dichloromethane for 1h; Reflux; Inert atmosphere;	98%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3)

Conditions	Yield
With pyridine; thionyl chloride In dichloromethane for 14h; Inert atmosphere; Reflux;	97%
With thionyl chloride In N,N-dimethyl-formamide at 28 - 60℃; for 3h;	95.2%
With pyridine; thionyl chloride In chloroform for 3h; Heating;	92%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + isocyanate de phenoxysulfonyle (14773-85-4) → (2-[2-methoxyethoxy]ethyl)-N-(phenoxysulfonyl)carbamate

Conditions	Yield
at 20℃; for 0.5h;	97%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)oxirane (38565-53-6) → 12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19,19-heptadecafluoro-2,5,8-trioxanonadecan-10-ol (1185746-42-2)

Conditions	Yield
With boron trifluoride diethyl etherate at 100℃; for 10h; Inert atmosphere; regioselective reaction;	97%

Adipic acid (124-04-9) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + Diethylene glycol monobutyl ether (112-34-5) → methyldiglycol butyldiglycol adipate

Conditions	Yield
toluene-4-sulfonic acid In toluene at 118 - 145℃; for 6.5h; Heating / reflux;	96.9%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + acrylonitrile (107-13-1) → 3-(2-(2-methoxyethoxy)ethoxy)propanenitrile (35633-45-5)

Conditions	Yield
With potassium hydroxide at 0℃; for 2h; Michael addition; Inert atmosphere;	96%
With sodium hydroxide In water at 25℃; for 6h; Michael Addition;	96%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 2-(2-methoxyethoxy)acetic acid (16024-56-9)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate; sodium carbonate at 20℃; for 2.5h; Electrochemical reaction;	96%
Stage #1: 2-(2-methoxyethoxy)ethyl alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium carbonate at 20℃; for 2h; aq. buffer; Electroliysis; Stage #2: With Amberlite IR 120 for 0.5h; aq. buffer;	96%
With chromium(VI) oxide
With Jones reagent In acetone at 20℃;
With oxygen In water at 80℃; under 6000.6 Torr; for 20h; pH=11; Autoclave;

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 4-(4,6-diphenoxy-1,3,5-triazine-2-yl)-4-benzylmorpholinium trifluoromethanesulfonate → diethylene glycol benzyl methyl diether

Conditions	Yield
With magnesium oxide In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere;	96%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 2-phenylquinoline-4-carbonyl chloride (59661-86-8) → C21H21NO4

Conditions	Yield
Schlenk technique;	96%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + Ricinoleic acid (141-22-0) → ricinoleic acid diethylene glycol monomethyl ether ester

Conditions	Yield
With sodium hydrogensulfate monohydrate In dichloromethane at 150℃; for 0.416667h; Microwave irradiation; High pressure;	96%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → [2-(2-Methoxy-ethoxy)-ethoxy]-dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silane (142992-74-3)

Conditions	Yield
With pyridine In diethyl ether Ambient temperature;	95%

Upstream product

• 90-15-3 α-naphthol 
• 67834-62-2 OO-tert-butyl methoxyethoxyethyl monoperoxycarbonate 
• 75-21-8 oxirane 
• 67-56-1 methanol 
• 109-86-4 2-methoxy-ethanol 
• 107-07-3 2-chloro-ethanol 
• 115319-74-9 4-hydroxybenzyl 2-(2-methoxyethoxy)ethyl ether 
• 222634-34-6 ethyl 2-(1-(1-imidazolylcarbonyloxy)-2-methylpropyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate 
• 112-35-6 triethylene glucol monomethyl ether 
• 111-46-6 diethylene glycol 
• 13752-97-1 3-<2-(2-Methoxyethoxy)ethoxy>propen 
• 66854-10-2 1,1-bis-[2-(2-methoxy-ethoxy)-ethoxy]-ethane 
• 40835-42-5 bis(methoxyethoxyethyl) peroxydicarbonate 
• 81194-70-9 C₂₃H₃₂O₆ 

Downstream Products

• 136814-65-8 1-(2-(2-methoxyethoxy)ethoxy)-2-nitrobenzene 
• 90335-39-0 benzoic acid 2-(2-methoxy-ethoxy)-ethyl ester 
• 50586-80-6 toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester 
• 210093-61-1 3-Bromo-5-{4-[2-(2-methoxy-ethoxy)-ethoxymethyl]-phenyl}-2-methyl-thiophene 
• 159821-59-7 2-bromo-3-(2,5,8-trioxanonyl)thiophene 
• 131841-09-3 hexakis[2-(2-methoxyethoxy)ethoxy]cyclotriphosphazene 
• 531521-23-0 3-[(2-(2-methoxyethoxy)ethoxy)methyl]-3-methyloxetane 
• 205193-35-7 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline hydrochloride 
• 6281-98-7 2-(2-methoxyethoxy)ethyl 2-bromoacetate 
• 82-45-1 1-amino-9,10-anthracenedione 
• 908592-64-3 C₆H₅B(OCH₂CH₂OCH₂CH₂OCH₃)2 
• 329946-02-3 2-methyl-4-[(2-{[2-(methyloxy)ethyl]oxy}ethyl)oxy]-1-nitrobenzene 
• 694-85-9 1-methyl-2-pyridone 

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Sensitivity improvement in hydrophilic interaction chromatography negative mode electrospray ionization mass spectrometry using 2-(2-methoxyethoxy)ethanol as a post-column modifier for non-targeted metabolomics☆08/20/2019

The application of ammonia acetate buffered liquid chromatography (LC) eluents is known to concomitantly lead to ion suppression when electrospray ionization mass spectrometry (ESI–MS) detection is used. In negative ESI mode, post column infusion of 2-(2-methoxyethoxy)ethanol (2-MEE) was shown ...detailed

Relevant articles and documents

Competitive RO-6 Neighboring Group Participation and Solvent-Assisted Displacement with 2-(2-Methoxyethoxy)ethyl Tosylate

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Lewis Base Catalyzed Selective Chlorination of Monosilanes

A preparatively facile, highly selective synthesis of bifunctional monosilanes R2SiHCl, RSiHCl2 and RSiH2Cl is reported. By chlorination of R2SiH2 and RSiH3 with concentrated HCl/ether solutions, the stepwise introduction of Si?Cl bonds is readily controlled by temperature and reaction time for a broad range of substrates. In a combined experimental and computational study, we establish a new mode of Si?H bond activation assisted by Lewis bases such as ethers, amines, phosphines, and chloride ions. Elucidation of the underlying reaction mechanisms shows that alcohol assistance through hydrogen-bond networks is equally efficient and selective. Remarkably, formation of alkoxysilanes or siloxanes is not observed under moderate reaction conditions.

Influence of Boiling on the Radiolysis of Diglyme

The radiolysis of diethylene glycol dimethyl ether (diglyme) in a boiling state has been studied for the first time. Boiling facilitates the cleavage of internal C–O bonds, weakens the cage effect and diglyme regeneration processes, and facilitates the exchange and dimerization reactions of radicals. As compared with radiolysis at room temperature, the amount of unsaturated products of diglyme fragmentation formed during irradiation in the boiling state is smaller by a factor of 4, and the disproportionation products of heavy radicals are found in negligible amounts, if any. The yield of radiolytic decomposition of diglyme under boiling conditions is ～15 molecule/100 eV, which is higher than that at room temperature by a factor of almost 1.5.