111-90-0

Basic information

• Product Name: Diethylene Glycol Monoethyl Ether
• Synonyms: 2,2’-oxybis-ethanomonoethylether;-2-Ethoxyethoxy;3,6-Dioxa-1-octanol;3,6-Dioxa-1-oktanol;3,6-Dioxaoctan-1-ol;3-Oxapentane-1,5-diolethylether;aethyldiaethylenglycol;Carbitol cellosolve
• CAS NO: 111-90-0
• Molecular Formula: C₆H₁₄O₃
• Molecular Weight: 134.17
• EINECS: 203-919-7
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols;ACS and Reagent Grade Solvents;Amber Glass Bottles;Carbon Steel Cans with NPT Threads;ReagentPlus;ReagentPlus Solvent Grade Products;Semi-Bulk Solvents;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;Reagent;organic intermediates
• Mol File: 111-90-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: -80 °C
• Boiling Point: 202 °C(lit.)
• Flash Point: 205 °F
• Appearance: Clear colorless/Liquid
• Density: 0.999 g/mL at 25 °C(lit.)
• Vapor Density: 4.63 (vs air)
• Vapor Pressure: 0.12 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: water: soluble
• PKA: 14.37±0.10(Predicted)
• Explosive Limit: 1.8-12.2%(V)
• Water Solubility: Miscible
• Sensitive: Hygroscopic
• Stability: Stable. Combustible. Note wide explosion limits. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid a
• Merck: 14,1800
• BRN: 1736441
• CAS DataBase Reference: Diethylene Glycol Monoethyl Ether(CAS DataBase Reference)
• NIST Chemistry Reference: Diethylene Glycol Monoethyl Ether(111-90-0)
• EPA Substance Registry System: Diethylene Glycol Monoethyl Ether(111-90-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36-20-36/37/38
• Safety Statements: 23-24/25-39-26-36
• WGK Germany: 1
• RTECS: KK8750000
• TSCA: Yes
• Hazardous Substances Data: 111-90-0(Hazardous Substances Data)

Usage

Definition

ChEBI: A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.

Safety Profile

irritation, and unspecified eye effects, cough,

Preparation

From ethyl alcohol plus ethylene oxide (Arctander, 1969).

Air & Water Reactions

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

General Description

A colorless, slightly viscous liquid with a mild pleasant odor. Flash point near 190°F. Used to make soaps, dyes, and other chemicals.

Health Hazard

None expected.

Chemical Properties

Diethylene glycol monoethyl ether is a colorless, stable, hygroscopic liquid of a mild, pleasant odor. It is completely miscible with water, alcohols, ethers, ketones, aromatic and aliphatic hydrocarbons, and halogenated hydrocarbons. Owing to the fact that it contains an ether-alcohol-hydrocarbon group in the molecule, it has the power to dissolve a wide variety of substances such as oils, fats, waxes, dyes, camphor and natural resins like copal resin, kauri, mastic, rosin, sandarac, shellac, as well as several types of synthetic resins. It is used as a solvent in synthetic resin coating compositions, and in lacquers, where high-boiling solvents are desired.

Metabolism

The major part of an administered dose of diethylene glycol monoethyl ether is oxidized in the body or excreted as the glucuronate, administration to rabbits orally or by sc injection being followed by a marked increase in the urinary content of glucuronic acid (Fellows, Luduena & Hanzlik, 1947).

Occurrence

Has apparently not been reported to occur in nature.

Chemical Reactivity

Reactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: V; Inhibitor of Polymerization: Not pertinent.

Reactivity Profile

Mixing 2(2-Ethoxyethoxy)ethanol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid and oleum, NFPA 1991.

Uses

Usually used as solvent for the polymer electrospinning.

Purification Methods

Ethylene glycol can be removed by extracting 250g in 750mL of *benzene with 5mL portions of water, allowing for phase separation, until successive aqueous portions show the same volume increase. Dry, and free from peroxides, as described for diethylene glycol mono-n-butyl ether. [Beilstein 1 IV 2393.]

Fire Hazard

2(2-Ethoxyethoxy)ethanol is combustible.

InChI:InChI=1/C4H10O3.C4H10O/c5-1-3-7-4-2-6;1-3-5-4-2/h5-6H,1-4H2;3-4H2,1-2H3

Synthetic route

trimethylsilyl 2-[2-(2-ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate (197356-81-3) → ethoxyethoxyethanol (111-90-0) + Carbitol-trimethylsilylaether (16654-46-9) + Sodium; 2-[2-(2-ethoxy-ethoxy)-ethoxy]-2,3,3,3-tetrafluoro-propionate

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water for 1h; Ambient temperature;	A n/a B n/a C 95%

oxirane (75-21-8) + 2-ethoxy-ethanol (110-80-5) → ethoxyethoxyethanol (111-90-0)

Conditions	Yield
With tungsten(VI) oxide at 90 - 95℃; unter Druck;
With sulfur dioxide at 75 - 80℃;

oxirane (75-21-8) + ethanol (64-17-5) → 2-ethoxy-ethanol (110-80-5) + ethoxyethoxyethanol (111-90-0)

Conditions	Yield
With sulfuric acid at 100 - 130℃; im Autoklaven;
With toluene-4-sulfonic acid at 100 - 130℃;
With 2,3-Dimethylaniline at 100 - 130℃;
With sulfuric acid at 80 - 100℃;
With metal oxide at 100 - 130℃;

ethyl bromide (74-96-4) + diethylene glycol (111-46-6) → ethoxyethoxyethanol (111-90-0)

Conditions	Yield
(i) Na, (ii) /BRN= 1209224/; Multistep reaction;

chloro-trimethyl-silane (75-77-4) + 2-[2-(2-Ethoxy-ethoxy)-ethoxy]-2,3,3,3-tetrafluoro-propionic acid 2-(2-ethoxy-ethoxy)-ethyl ester (197356-78-8) → ethoxyethoxyethanol (111-90-0) + Carbitol-trimethylsilylaether (16654-46-9) + trimethylsilyl 2-[2-(2-ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate (197356-81-3)

Conditions	Yield
With sodium hydroxide; sodium hydride 1.) H2O, THF, 40 deg C, 3 h, 2.) Et2O, room temp., 3 h; Multistep reaction. Yields of byproduct given;
With sodium hydroxide; sodium hydride 1.) H2O, THF, 40 deg C, 3 h, 2.) Et2O, room temp., 3 h; Yield given. Multistep reaction;

2-[2-(2-Ethoxy-ethoxy)-ethoxy]-2,3,3,3-tetrafluoro-propionic acid 2-(2-ethoxy-ethoxy)-ethyl ester (197356-78-8) → ethoxyethoxyethanol (111-90-0) + 2-(2-ethoxyethoxy)ethyl trifluoroacetate

Conditions	Yield
With sodium hydroxide 1.) THF, H2O, 40 deg C, 3 h, 2.) 200 deg C; Yield given. Multistep reaction;

oxirane (75-21-8) + 2-ethoxy-ethanol (110-80-5) + H2WO4 → ethoxyethoxyethanol (111-90-0)

Conditions	Yield
at 90 - 95℃; under 7355.08 - 8826.09 Torr;

diethylene glycol monoethyl ether acetate (112-15-2) → ethoxyethoxyethanol (111-90-0) + acetic acid (64-19-7)

Conditions	Yield
With hydrogenchloride; water at 30 - 49.8℃; Kinetics;

ethoxyethoxyethanol (111-90-0) + p-toluenesulfonyl chloride (98-59-9) → 2-(2-ethoxyethoxy)ethyl tosylate (54176-27-1)

Conditions	Yield
With pyridine at 5℃;	100%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Inert atmosphere;	98%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 1.16667h; Inert atmosphere;	95.8%

ethoxyethoxyethanol (111-90-0) + methyl (E)-m-fluorocinnamate (74325-03-4) → Methyl 2-(3-fluorophenyl)cyclopropanecarboxylate

Conditions	Yield
Stage #1: ethoxyethoxyethanol With N-methyl-N-nitrosotoluene-p-sulfonamide; potassium hydroxide In diethyl ether; water at 65℃; Stage #2: methyl (E)-m-fluorocinnamate; palladium diacetate In diethyl ether; dichloromethane; water at 0 - 20℃; for 2.5h;	100%
With potassium hydroxide; palladium diacetate In dichloromethane; water

cycl-isopropylidene malonate (2033-24-1) + ethoxyethoxyethanol (111-90-0) → 2-(2-ethoxyethoxy)ethyl hydrogen propanedioate

Conditions	Yield
at 120℃; for 3h;	99%
at 120℃; for 3h;	82%
at 110 - 120℃; for 3h; Yield given;

ethoxyethoxyethanol (111-90-0) + 1,2-dibromomethane (74-95-3) → 1,13-diethoxy-3,6,8,11-tetraoxa-tridecane (42598-91-4)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water; chlorobenzene at 50℃; for 0.5h;	98.58%

ethoxyethoxyethanol (111-90-0) + Methyl decanoate (110-42-9) → 1-Decanol (112-30-1)

Conditions	Yield
With sodium borohydrid In 5,5-dimethyl-1,3-cyclohexadiene	97%

3-benzyl-6-bromo-2-chloro-quinoline (654655-68-2) + ethoxyethoxyethanol (111-90-0) → C22H24BrNO3 (918519-43-4)

Conditions	Yield
Stage #1: ethoxyethoxyethanol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 3-benzyl-6-bromo-2-chloro-quinoline In tetrahydrofuran at 0℃; for 18h; Heating / reflux;	97%

4,4'-dibromo-2,2'-bipyridine (18511-71-2) + ethoxyethoxyethanol (111-90-0) → 4,4′-bis[2-(2-ethoxyethoxy)ethoxy]-2,2′-bipyridine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;	97%

ethoxyethoxyethanol (111-90-0) + C11H22N2OZn → C15H30N2O4Zn

Conditions	Yield
In toluene at -20 - 20℃; for 8h; Temperature; Schlenk technique;	97%

benzoic acid methyl ester (93-58-3) + ethoxyethoxyethanol (111-90-0) → 2-(2-ethoxyethoxy)ethyl benzoate (90327-11-0)

Conditions	Yield
With N-methyl-N,N,N-trioctylammonium methylcarbonate In hexane for 3h; Molecular sieve; Reflux; Green chemistry;	96%

ethoxyethoxyethanol (111-90-0) + methanesulfonyl chloride (124-63-0) → 2-(2-ethoxyethoxy)ethyl methanesulfonate (203568-17-6)

Conditions	Yield
Stage #1: ethoxyethoxyethanol With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: methanesulfonyl chloride In dichloromethane at 0 - 20℃; Inert atmosphere;	95%
With triethylamine In dichloromethane at 0 - 20℃; for 72h; Inert atmosphere;

ethoxyethoxyethanol (111-90-0) → 1-[2-(ethoxy)ethoxy]-2-chloroethane (41771-35-1)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide	94%
With pyridine; thionyl chloride
With thionyl chloride; pyrographite for 14h; Heating;

ethoxyethoxyethanol (111-90-0) + hydroxy L-proline (618-27-9) → chlorhydrate de la carbethoxy-2-ethoxyhydroxyproline

Conditions	Yield
With thionyl chloride 2 h, room t., 90 min, reflux;	93%

ethoxyethoxyethanol (111-90-0) + 3-chloro-3-(p-nitrophenyl)diazirine (39184-67-3) → 2-chloroethyl ethyl ether (628-34-2) + 2-(4-nitrophenyl)-1,3-dioxolane (2403-53-4) + 1-dichloromethyl-4-nitrobenzene (619-78-3)

Conditions	Yield
at 80℃; for 6h;	A n/a B 93% C n/a

poly(methacrylic acid) (79-41-4) + ethoxyethoxyethanol (111-90-0) → di(ethylene glycol) ethyl ether methacrylate (45127-97-7)

Conditions	Yield
With 10H-phenothiazine In toluene at 155℃; Temperature;	92.49%

ethoxyethoxyethanol (111-90-0) + thioacetic acid (507-09-5) → S-acetyl 3,6-dioxooctanethiol (294201-62-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1.5h; thioacetylation;	91%

ethoxyethoxyethanol (111-90-0) + cyanoacetic acid (372-09-8) → diethylene glycol ethyl ether cyanoacetate (32804-82-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 2h;	90%
With sulfuric acid In toluene
With toluene-4-sulfonic acid In toluene at 20℃; Reflux;

ethoxyethoxyethanol (111-90-0) + 1,2-Diiodobenzene (615-42-9) → 1,2-bis(2-(2-ethylethoxy)ethoxy)benzene (57721-94-5)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Reflux; Inert atmosphere;	90%

ethoxyethoxyethanol (111-90-0) + carbonochloridic acid 1-chloro-ethyl ester (50893-53-3) → 1-chloroethyl (2-(2-ethoxyethoxy)ethyl) carbonate (117971-96-7)

Conditions	Yield
With pyridine In dichloromethane at -78℃; for 3h;	89%
With pyridine In dichloromethane at -78℃; for 3h;	89%

ethoxyethoxyethanol (111-90-0) + 2-Bromoacetyl bromide (598-21-0) → 2-(2-ethoxyethoxy)ethyl 2-bromoacetate (56521-77-8)

Conditions	Yield
With aluminum oxide at 0 - 20℃; for 1h; Product distribution / selectivity;	88%
With triethylamine In dichloromethane at -78℃; for 3h; Product distribution / selectivity;	71%
With triethylamine In dichloromethane at -78℃; Inert atmosphere;	61%

ethoxyethoxyethanol (111-90-0) + D-glucal triacetate (2873-29-2) → 2-(2-ethoxyethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside + 2-(2-ethoxyethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

Conditions	Yield
With tellurium tetrachloride In dichloromethane at 0 - 20℃; for 0.333333h; Ferrier Carbohydrate Rearrangement; Inert atmosphere; diastereoselective reaction;	A 88% B n/a

ethoxyethoxyethanol (111-90-0) + 2,2-dimethylpropanoic anhydride (1538-75-6) → 2-(2-ethoxyethoxy)ethyl pivalate

Conditions	Yield
With phosphoric acid In acetonitrile for 24h; Reflux;	88%

ethoxyethoxyethanol (111-90-0) → 1-bromo-2-(2-ethoxyethoxy)ethane (54550-36-6)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	87%
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 12h;	87%
With pyridine; phosphorus tribromide In benzene for 56h;	65%
With pyridine; phosphorus tribromide

ethoxyethoxyethanol (111-90-0) + 5-aminolevulinic acid hydrochloride (5451-09-2) → 3,6-Dioxa-1-octyl 5-amino-4-oxopentanoate Hydrochloride

Conditions	Yield
With thionyl chloride at 50℃; for 5h;	87%
	0.90 g (53%)

ethoxyethoxyethanol (111-90-0) + 4-Vinylbenzyl chloride (1592-20-7) → 1-((2-(2-ethoxyethoxy)ethoxy)methyl)-4-vinylbenzene

Conditions	Yield
Stage #1: ethoxyethoxyethanol With sodium hydride In tetrahydrofuran at 0℃; for 2h; Stage #2: 4-Vinylbenzyl chloride In tetrahydrofuran for 24h; Reflux;	87%

ethoxyethoxyethanol (111-90-0) + 5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[4,5-g]quinoline-7-carbonyl chloride (19658-59-4) → 5-Ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid 2-(2-ethoxy-ethoxy)-ethyl ester (113485-69-1)

Conditions	Yield
With pyridine In dichloromethane for 3h;	85%

6-amino-7-methoxy-4-(3'-methylanilino)quinazoline (153437-17-3) + ethoxyethoxyethanol (111-90-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloro-3,4-dihydroquinazolin-4-one (31374-18-2)

Conditions	Yield
With formamide	85%

6-nitro-7-chloro-4-(3-methylanilino)quinazoline (161830-29-1) + ethoxyethoxyethanol (111-90-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloroquinazolin-4(1H)-one (31374-18-2)

Conditions	Yield
With formamide	85%
With formamide	85%

6-amino-7-methoxy-4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]quinazoline (179688-72-3) + ethoxyethoxyethanol (111-90-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloroquinazolin-4(1H)-one (31374-18-2)

Conditions	Yield
With formamide	85%

4,7-dichloroquinazoline (2148-57-4) + ethoxyethoxyethanol (111-90-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloroquinazolin-4(1H)-one (31374-18-2)

Conditions	Yield
With formamide	85%

Upstream product

• 111-46-6 Diethylene glycol 
• 64-67-5 Diethyl sulfate 
• 64-17-5 Etanol 

Downstream Products

• 112-36-7 2-Ethoxyethyl ether 
• 7169-37-1 7-METHOXY-3(2H)-BENZOFURANONE 

Recommend Products

• 75-21-8  oxirane 
• 110-80-5  2-ethoxy-ethanol 
• 64-17-5  ethanol 
• 112-50-5  monoethyl ether of triethylene glycol 
• 5650-20-4  3,6,9,12-tetraoxatetradecan-1-ol 
• 3895-17-8  2-butoxyethyl 2-ethoxyethyl ether 
• 109-65-9  1-bromo-butane 
• 53404-36-7  (2,4-dichloro-phenoxy)-acetic acid-[2-(2-ethoxy-ethoxy)-ethyl ester] 
• 94-75-7  2,4-Dichlorophenoxyacetic acid 
• 42598-91-4  Di-<2-(2-ethoxyethoxy)-ethoxy>-methan 
• 75-09-2  dichloromethane 
• 75888-21-0  tris-(3,6-dioxa-octyl)amine 
• 77455-70-0  9-aza-3,6,12,15-tetraoxaheptadecane 
• 1745-81-9  o-Allylphenol 

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