112-50-5

Basic information

• Product Name: Triethylene glycol monoethyl ether
• Synonyms: TRI(ETHYLENE GLYCOL) MONOETHYL ETHER, T&;Ethanol, 2-2-(2-ethoxyethoxy)ethoxy-;3,6,9-TRIOXA-1-UNDECANOL;ETHANOL,2-[2-(2-ETHOXYETHOXY);Triethylenehydrol ethyl ester;ethylene triglycol;Tri(ethylene glycol) monoethyl ether technical grade;TRIGLYCOL MONOETHYL ETHER
• CAS NO: 112-50-5
• Molecular Formula: C₈H₁₈O₄
• Molecular Weight: 178.23
• EINECS: 203-978-9
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols
• Mol File: 112-50-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: -19°C(lit.)
• Boiling Point: 256 °C(lit.)
• Flash Point: >230 °F
• Appearance: Odorless colorless liquid
• Density: 1.020 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00238mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Solubility: Completely miscible in water
• PKA: 14.36±0.10(Predicted)
• Water Solubility: 1.02g/L at 20℃
• BRN: 1700466
• CAS DataBase Reference: Triethylene glycol monoethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylene glycol monoethyl ether(112-50-5)
• EPA Substance Registry System: Triethylene glycol monoethyl ether(112-50-5)

Safety Data

• RTECS: KK8950000
• F: 10-23
• Hazardous Substances Data: 112-50-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid. Combustible.

Uses

Chemical intermediate.

General Description

Odorless colorless liquid. Sinks and mixes with water.

Air & Water Reactions

Water soluble.

Reactivity Profile

Triethylene glycol monoethyl ether is a ethoxy-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.

Safety Profile

Mildly toxic by ingestion and slm contact. An eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. Tofight fire, use foam, alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

InChI:InChI=1/C8H18O4/c1-2-10-5-6-12-8-7-11-4-3-9/h9H,2-8H2,1H3

Synthetic route

2-(2-(2-(2-iodoethoxy)ethoxy)ethoxy)ethanol (136399-06-9) → monoethyl ether of triethylene glycol (112-50-5)

Conditions	Yield
With tri(2-furyl)germane; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile In water at 80℃; for 1h;	97%

ethyl iodide (75-03-6) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → monoethyl ether of triethylene glycol (112-50-5)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 4h; Ambient temperature;	60%

oxirane (75-21-8) + ethanol (64-17-5) → monoethyl ether of triethylene glycol (112-50-5)

Conditions	Yield
With sulfuric acid at 80 - 100℃;

oxirane (75-21-8) + ethoxyethoxyethanol (111-90-0) → monoethyl ether of triethylene glycol (112-50-5)

Conditions	Yield
With ethanolamine at 50 - 60℃;

oxirane (75-21-8) + ethoxyethoxyethanol (111-90-0) → monoethyl ether of triethylene glycol (112-50-5) + 3,6,9,12-tetraoxatetradecan-1-ol (5650-20-4)

Conditions	Yield
With ethanolamine at 50 - 60℃;

oxirane (75-21-8) + ethoxyethoxyethanol (111-90-0) + ethanolamine (141-43-5) → monoethyl ether of triethylene glycol (112-50-5) + 3,6,9,12-tetraoxatetradecan-1-ol (5650-20-4)

Conditions	Yield
at 50 - 63℃;

ethoxyethoxyethanol (111-90-0) + 2-chloro-ethanol (107-07-3) → monoethyl ether of triethylene glycol (112-50-5)

Conditions	Yield
at 70 - 80℃; reagiert das Natriumsalz;

ethyl bromide (74-96-4) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → monoethyl ether of triethylene glycol (112-50-5)

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

2-chloro-ethanol (107-07-3) + sodium salts of diethylene glycol-monoethyl ether → monoethyl ether of triethylene glycol (112-50-5)

Conditions	Yield
at 70 - 80℃;

oxirane (75-21-8) + ethanol (64-17-5) → monoethyl ether of triethylene glycol (112-50-5) + 2-ethoxy-ethanol, O-ethyl-diethylene glycol

Conditions	Yield
With sodium ethanolate

monoethyl ether of triethylene glycol (112-50-5) + p-toluenesulfonyl chloride (98-59-9) → 2-(2-(2-ethoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (62921-75-9)

Conditions	Yield
With triethylamine at 0 - 20℃;	100%
Stage #1: monoethyl ether of triethylene glycol; p-toluenesulfonyl chloride With dmap In dichloromethane at 20℃; Stage #2: With triethylamine In dichloromethane at 20℃;	100%
With pyridine at 0 - 20℃; for 2h; Tosylation;	97%

hydrogenchloride (7647-01-0) + monoethyl ether of triethylene glycol (112-50-5) + p-toluenesulfonyl chloride (98-59-9) → 2-(2-(2-ethoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (62921-75-9)

Conditions	Yield
Stage #1: monoethyl ether of triethylene glycol; p-toluenesulfonyl chloride With pyridine In diethyl ether for 3.5h; Cooling with ice; Stage #2: hydrogenchloride In water; ethyl acetate	100%

monoethyl ether of triethylene glycol (112-50-5) + Methyl decanoate (110-42-9) → 1-Decanol (112-30-1)

Conditions	Yield
With sodium borohydrid In 5,5-dimethyl-1,3-cyclohexadiene	99%

monoethyl ether of triethylene glycol (112-50-5) → 2-(2-(2-ethoxyethoxy)ethoxy)ethan-1-amine

Conditions	Yield
With 1% Pd on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 24h;	97%
Multi-step reaction with 3 steps 1.1: dmap / dichloromethane / 20 °C 1.2: 20 °C 2.1: N,N-dimethyl-formamide / 18 h / 80 °C 3.1: hydrazine hydrate / ethanol / 3 h / 76 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / tetrahydrofuran; water / 2.25 h / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere 3: hydrazine hydrate / ethanol / 110 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / tetrahydrofuran; water / 4 h / 0 - 20 °C 2: N,N-dimethyl-formamide / 16 h / Heating 3: hydrazine hydrate / ethanol / 16 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / tetrahydrofuran; water / 0.25 h / 0 - 20 °C 1.2: 16 h / 0 - 20 °C 2.1: N,N-dimethyl-formamide / 16 h / 20 - 110 °C 3.1: hydrazine hydrate / ethanol / 16 h / 110 °C View Scheme

monoethyl ether of triethylene glycol (112-50-5) + Boc-Glu (2419-94-5) → C26H49NO12 (1421470-02-1)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -10 - 20℃; for 8h;	95%

monoethyl ether of triethylene glycol (112-50-5) + ethyl acrylate (140-88-5) → ethyl 4,7,10,13-tetroxapentadecanoate (257941-17-6)

Conditions	Yield
With sodium ethanolate In ethanol; toluene for 48h; Addition; Heating;	94%

monoethyl ether of triethylene glycol (112-50-5) + acrylonitrile (107-13-1) → 3,6,9,12-tetraoxapentadecane-15-nitrile

Conditions	Yield
With sodium methylate at 60℃; for 0.166667h;	92%

monoethyl ether of triethylene glycol (112-50-5) + 5-aminolevulinic acid hydrochloride (5451-09-2) → 5-amino-4-oxo-pentanoic acid 2-[2-(2-ethoxy-ethoxy)-ethoxy]-ethyl ester; hydrochloride

Conditions	Yield
With thionyl chloride at 50℃; for 5h;	90%

monoethyl ether of triethylene glycol (112-50-5) → 2-[2-(2-ethoxyethoxy)ethoxy]ethyl chloride (538371-55-0)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide	89%
With thionyl chloride In toluene at 90℃; for 24h;	57%

monoethyl ether of triethylene glycol (112-50-5) + 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (131986-28-2) → tri(ethylene glycol) ethyl[3-(pyrid-3-yl)-1,2,5-thiadiazol-4-yl]ether (615284-12-3)

Conditions	Yield
Stage #1: monoethyl ether of triethylene glycol With sodium hydride In tetrahydrofuran Heating; Stage #2: 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine In tetrahydrofuran Heating;	88.4%

monoethyl ether of triethylene glycol (112-50-5) + 3-Phenylpropionic acid (501-52-0) → 3-phenyl-propionic acid 2-[2-(2-ethoxy-ethoxy)-ethoxy]-ethyl ester

Conditions	Yield
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h;	88%

monoethyl ether of triethylene glycol (112-50-5) + 3-chloroprop-1-ene (107-05-1) → 4,7,10,13-tetraoxapentadecene

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water at 30 - 45℃;	88%

monoethyl ether of triethylene glycol (112-50-5) + 2-allyloxy-1,2-oxaborolane (79363-73-8) → 2-(2-ethoxy-2-ethoxy-2-ethoxyethoxy)-1,2-oxaborolane (129585-03-1)

Conditions	Yield
In neat (no solvent) byproducts: allyl alcohol; N2 atmosphere; stirring and heating (160-180°C, 2 h); distn. of allyl alcohol (atmospheric pressure), distn. (vac.); elem. anal.;	86.7%

monoethyl ether of triethylene glycol (112-50-5) + 3-(tert-butyldimethylsilyloxy)glutaric anhydride (91424-40-7) → C19H38O8Si (1345718-76-4)

Conditions	Yield
In toluene for 16h; Reflux;	81%

monoethyl ether of triethylene glycol (112-50-5) + bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl dichloride → endo,exo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis[2-[2-(2-ethoxyethoxy)ethoxy]ethyl] ester

Conditions	Yield
With pyridine; dmap In dichloromethane Inert atmosphere;	80%

4,4'-dibromo-2,2'-bipyridine (18511-71-2) + monoethyl ether of triethylene glycol (112-50-5) → 4,4′-di{2-[2-(2-ethoxyethoxy)ethoxy]ethoxy}-2,2′-bipyridine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;	77%

monoethyl ether of triethylene glycol (112-50-5) + 2,7-dinitro-9H-fluorene-4-carbonyl chloride (226419-16-5) → 2,7-dinitrofluorene-4-carboxylic acid (triethylene glycol monoethyl ether) ester (226419-19-8)

Conditions	Yield
at 90 - 100℃; for 0.0833333h;	73%

monoethyl ether of triethylene glycol (112-50-5) + 1,3-Diiodobenzene (626-00-6) → 1,3-bis(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzene (1195761-44-4)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Reflux; Inert atmosphere;	71%

monoethyl ether of triethylene glycol (112-50-5) + Dimethyl phosphite (868-85-9) → 2-(2-(2-ethoxyethoxy)ethoxy)ethyl methyl phosphonate

Conditions	Yield
With zinc(II) acetylacetonate at 0℃; for 18h; Molecular sieve; Sealed tube; Inert atmosphere;	71%

monoethyl ether of triethylene glycol (112-50-5) + bromoacetic acid (79-08-3) → 3,6,9,12-Tetraoxatetradecansaeure (5650-19-1)

Conditions	Yield
With sodium hydride; potassium iodide In tetrahydrofuran at 0 - 5℃; for 12.5h; Inert atmosphere;	70%

monoethyl ether of triethylene glycol (112-50-5) + N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine (19746-37-3) → C19H36N2O8S

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	67%

12-aza-3,6,9,15,18,21-hexaoxa-tricosane + monoethyl ether of triethylene glycol (112-50-5) → tris-(3,6,9-trioxaundecyl)-amine

Conditions	Yield
aluminum nickel	66%

monoethyl ether of triethylene glycol (112-50-5) + 1,2-Diiodobenzene (615-42-9) → 1,2-bis(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzene

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Reflux; Inert atmosphere;	61%

monoethyl ether of triethylene glycol (112-50-5) + acryloyl chloride (814-68-6) → 3,6,9-trioxaundecyl acrylate

Conditions	Yield
With triethylamine In tetrahydrofuran	60%

monoethyl ether of triethylene glycol (112-50-5) + C21H19ClNO4P → 3,6,9-trioxaundecyl phenyl (benzyloxycarbonylamino)(phenyl)methylphosphonate

Conditions	Yield
for 3h; Reflux;	57.5%

monoethyl ether of triethylene glycol (112-50-5) + Adipic acid dichloride (111-50-2) → hexanedioic acid bis-{2-[2-(2-ethoxy-ethoxy)-ethoxy]-ethyl} ester

Conditions	Yield
With triethylamine for 1h;	57%

monoethyl ether of triethylene glycol (112-50-5) + cis-norbornene-endo-2,3-dicarboxylic acid (21196-51-0) → C25H42O10

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	57%

monoethyl ether of triethylene glycol (112-50-5) → 1-bromo-2-(2-(2-ethoxyethoxy)ethoxy)ethane (102684-61-7)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane for 16h; Ambient temperature;	54%

Upstream product

• 111-90-0 ethoxyethoxyethanol 
• 107-07-3 2-chloro-ethanol 
• 74-96-4 ethyl bromide 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 136399-06-9 2-(2-(2-(2-iodoethoxy)ethoxy)ethoxy)ethanol 
• 75-21-8 oxirane 
• 141-43-5 ethanolamine 
• 64-17-5 ethanol 
• 75-03-6 ethyl iodide 

Downstream Products

• 1195761-44-4 1,3-bis(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzene 
• 5650-19-1 3,6,9,12-Tetraoxatetradecansaeure 
• 1595067-42-7 C₃₉H₇₁BrO₁₆ 
• 1595067-40-5 C₃₉H₇₂O₁₇ 
• 1595067-38-1 C₄₀H₇₂O₁₈ 
• 1595067-36-9 C₂₃H₄₀O₁₀S 
• 1202396-89-1 2-(2-(2-(3,4,5-tris(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzyloxy)ethoxy)ethoxy)ethanol 
• 1104597-89-8 3,4,5-tris(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzyl chloride 
• 1096159-35-1 1-(hydroxymethyl)-3,4,5-tri{2-[2-(2-ethoxyethoxy)ethoxy]ethoxy}benzene 

Relevant articles and documents

Reduction of organic halides with tri-2-furylgermane: Stoichiometric and catalytic reduction

Tri-2-furylgermane proved to be an effective reagent for the radical reduction of organic halides. Treatment of 1-bromododecane with tri-2-furylgermane in THF at 25 °C in the presence of a catalytic amount of triethylborane afforded dodecane almost quantitatively. Radical cyclization of 2-iodoethanal allyl acetal afforded five-membered products under the same reaction conditions. These reactions proceeded with NaBH4 in the presence of a catalytic amount of germanium hydride. The reaction took place in water as well as in THF to give the corresponding reduced compounds in good yields.

Process for preventing consolidation of p-dichlorobenzene

A triethylene glycol derivative is added to p-dichlorobenzene so as to prevent consolidation and improve flowability of p-dichlorobenzene.