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: 2

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

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.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Different sources of media describe the Uses of 111-90-0 differently. You can refer to the following data:
1. Diethylene glycol monoethyl ether has low setting point and low viscocity at low temperature so it is used in manufacturing brake fluid. It is used as a flow and gloss promoter in paint industries, in production of printing ink and as a cleaner in offset printing. Also used in textile as a solvent for dyestuff in the printing and dying of fiber & fabrics, in the production & wood preservaties.
2. Di(ethylene glycol) ethyl ether is suitable for use as solvent for the polymer electrospinning.
3. Usually used as solvent for the polymer electrospinning.

Definition

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

Preparation

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

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.

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].

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.

Health Hazard

None expected.

Fire Hazard

2(2-Ethoxyethoxy)ethanol is combustible.

Safety Profile

irritation, and unspecified eye effects, cough,

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).

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.]

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

• 75-21-8 oxirane 
• 110-80-5 2-ethoxy-ethanol 
• 64-17-5 ethanol 
• 74-96-4 ethyl bromide 
• 111-46-6 diethylene glycol 
• 75-77-4 chloro-trimethyl-silane 
• 197356-78-8 2-[2-(2-Ethoxy-ethoxy)-ethoxy]-2,3,3,3-tetrafluoro-propionic acid 2-(2-ethoxy-ethoxy)-ethyl ester 
• 197356-81-3 trimethylsilyl 2-[2-(2-ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate 
• 112-15-2 diethylene glycol monoethyl ether acetate 

Downstream Products

• 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 
• 42598-91-4 Di-<2-(2-ethoxyethoxy)-ethoxy>-methan 
• 75888-21-0 tris-(3,6-dioxa-octyl)amine 
• 1745-81-9 o-Allylphenol 
• 13997-74-5 2-allyl-4-bromophenol 
• 6628-06-4 2-allyl-4-methylphenol 
• 13997-73-4 2-allyl-4-chlorophenol 
• 584-82-7 2-allyl-4-methoxyphenol 
• 19182-96-8 2-allyl-4-nitrophenol 
• 35736-25-5 3-(2-hydroxy-5-aminophenyl)-1-propene 
• 90923-69-6 3-allyl-4-hydroxy-benzonitrile 
• 21424-62-4 3-allyl-(1,1’-biphenyl)-4-ol 

Related news

Research paperEvaluation of the transepidermal permeation of Diethylene Glycol Monoethyl Ether (cas 111-90-0) and skin water loss08/25/2019

The rate of Transcutol® (TC)-water interchange, was studied using whole and stripped hairless rat skin in a modified vertical Franz diffusion cell. The presence of stratum corneum limited the passage of the two solvents, but after stripping of the skin, the rate of TC transfer increased and the ...detailed

Invited ReviewA review of the nonclinical safety of Transcutol®, a highly purified form of Diethylene Glycol Monoethyl Ether (cas 111-90-0) (DEGEE) used as a pharmaceutical excipient08/22/2019

Transcutol® (Diethylene glycol monoethyl ether, DEGEE), CAS # 111-90-0, is commonly used as a vehicle in the formulation or manufacturing process of pharmaceuticals, cosmetics, and food additives. This paper presents unpublished nonclinical safety data using a form of DEGEE which includes a sign...detailed

Density, Viscosity, and Excess Properties for Binary Mixture of Diethylene Glycol Monoethyl Ether (cas 111-90-0) + Water from 293.15 to 333.15 K at Atmospheric Pressure08/20/2019

Densities and viscosities were measured as a function of composition for binary liquid mixture of diethylene glycol monoethyl ether [CH3CH2O(CH2)2O(CH2)2OH] + water from 293.15 to 333.15 K at atmospheric pressure, with a capillary pycnometer and Ubbelohde capillary viscometer respectively. From ...detailed

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