4206-61-5

Basic information

• Product Name: DIETHYLENGLYKOL-DIGLYCIDYLETHER
• Synonyms: DIETHYLENGLYKOL-DIGLYCIDYLETHER;2,2’-(oxybis(2,1-ethanediyloxymethylene))bis-oxiran;2,2’-(oxybis(2,1-ethanediyloxymethylene))bisoxirane;2,2’-[oxybis(2,1-ethanediyloxy-methylene)]bis-Oxirane;diglycidyldiethyleneglycolether;ether,bis(2-(2,3-epoxypropoxy)ethyl);2,2'-[oxybis(ethyleneoxymethylene)]bisoxirane;diglycidyl diglycol
• CAS NO: 4206-61-5
• Molecular Formula: C₁₀H₁₈O₅
• Molecular Weight: 218.24692
• EINECS: 224-122-0
• Product Categories: Building Blocks;Chemical Synthesis;Epoxides;Organic Building Blocks;Oxygen Compounds;potting materials, special coatings, adhesives
• Mol File: 4206-61-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 278.93°C (rough estimate)
• Flash Point: 125 °C
• Appearance: /
• Density: 1.167 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.467
• CAS DataBase Reference: DIETHYLENGLYKOL-DIGLYCIDYLETHER(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYLENGLYKOL-DIGLYCIDYLETHER(4206-61-5)
• EPA Substance Registry System: DIETHYLENGLYKOL-DIGLYCIDYLETHER(4206-61-5)

Safety Data

• Statements: 19
• WGK Germany: 3
• RTECS: KN2330000
• F: 10-21
• Hazardous Substances Data: 4206-61-5(Hazardous Substances Data)

Usage

Contact allergens

Diethyleneglycol diglycidyl ether was contained in a reactive diethyleneglycol-based diluent of epoxy res- ins and caused contact dermatitis in three workers at a ski factory.

Synthetic route

bis(allyloxy)diethylene glycol (57947-82-7) → diethylene glycol diglycidyl ether (4206-61-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;	98%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h;

epichlorohydrin (106-89-8) + diethylene glycol (111-46-6) → diethylene glycol diglycidyl ether (4206-61-5)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 40℃; for 0.75h;	68%
With sodium hydroxide; tetrabutyl-ammonium chloride In water at 40℃; for 0.75h;	33.7%
Stage #1: diethylene glycol Stage #2: epichlorohydrin

diethylene glycol diglycidyl ether (4206-61-5) + ethane-1,2-dithiol (540-63-6) → C12H24O5S2 (1273318-55-0)

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide at 25℃; for 0.5h; Neat (no solvent); regiospecific reaction;	94%

diethylene glycol diglycidyl ether (4206-61-5) → 1,13-dihydrazino-4,7,10-trioxatridecane-2,12-diol

Conditions	Yield
With hydrazine hydrate In chloroform at 10℃; for 60h;	86%

diethylene glycol diglycidyl ether (4206-61-5) + hexan-1-amine (111-26-2) → 1-Hexylamino-3-{2-[2-(3-hexylamino-2-hydroxy-propoxy)-ethoxy]-ethoxy}-propan-2-ol (92237-83-7)

Conditions	Yield
at 120℃; for 4h;	85%

diethylene glycol diglycidyl ether (4206-61-5) + phenyl isocyanate (103-71-9) → 1,9-bis(3-phenyloxazolidin-2-on-5-yl)-2,5,8-trioxanonane

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With Tributylphosphine oxide; lithium bromide In toluene for 2h; Heating; Stage #2: phenyl isocyanate In toluene for 18h; Heating; Further stages.;	83%

diethylene glycol diglycidyl ether (4206-61-5) → C10H20N6O5

Conditions	Yield
With sodium azide; ammonium chloride In methanol; water at 80℃; for 24h;	83%
With sodium azide In methanol; water at 80℃;

diethylene glycol diglycidyl ether (4206-61-5) + n-butyl isocyanide (111-36-4) → 1,9-bis(3-butyloxazolidin-2-on-5-yl)-2,5,8-trioxanonane

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With Tributylphosphine oxide; lithium bromide In toluene for 2h; Heating; Stage #2: n-butyl isocyanide In toluene for 21h; Heating; Further stages.;	80%

carbon disulfide (75-15-0) + diethylene glycol diglycidyl ether (4206-61-5) → 1,9-bis(oxathiolane-2-thione-5-yl)-2,5,8-trioxanonane

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With lithium bromide In dichloromethane for 2h; Heating; Stage #2: carbon disulfide In dichloromethane for 16h; Heating; Further stages.;	79%

carbon disulfide (75-15-0) + diethylene glycol diglycidyl ether (4206-61-5) + phenyl isocyanate (103-71-9) → 5-(9-oxathiolan-2-thione-2,5,8-trioxanonan-5-yl)-3-phenyloxazolidin-2-one

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: phenyl isocyanate In tetrahydrofuran Inert atmosphere; Reflux; Stage #3: carbon disulfide In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	73%

diethylene glycol diglycidyl ether (4206-61-5) + 1-dodecyl alcohol (112-53-8) → 2-<(dodecyloxy)methyl>-12-hydroxy-13-crown-4

Conditions	Yield
With lithium at 60℃; for 20h;	72%

diethylene glycol diglycidyl ether (4206-61-5) + methylamine (74-89-5) → 1-{2-[2-(2-Hydroxy-3-methylamino-propoxy)-ethoxy]-ethoxy}-3-methylamino-propan-2-ol (344336-10-3)

Conditions	Yield
for 50h; Ambient temperature;	71%

diethylene glycol diglycidyl ether (4206-61-5) + ethylamine (75-04-7) → Bistetraethylene glycol (92237-86-0)

Conditions	Yield
In water for 50h; Ambient temperature;	70%

carbon disulfide (75-15-0) + diethylene glycol diglycidyl ether (4206-61-5) + Cyclohexyl isocyanate (3173-53-3) → 5-(6-oxathiolan-2-thione-2,5,8-trioxanonan-5-yl)-3-cyclohexyloxazolidin-2-one

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: Cyclohexyl isocyanate In tetrahydrofuran Inert atmosphere; Reflux; Stage #3: carbon disulfide In tetrahydrofuran at 20℃; for 13h; Inert atmosphere;	70%

diethylene glycol diglycidyl ether (4206-61-5) + phenyl isocyanate (103-71-9) → 5-(9-oxiran-2,5,8-trioxanonan-5-yl)-3-phenyloxazolidin-2-one

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: phenyl isocyanate In tetrahydrofuran for 8h; Inert atmosphere; Reflux;	68%

carbon disulfide (75-15-0) + diethylene glycol diglycidyl ether (4206-61-5) → 5-[9-oxiran-2,5,8-trioxanonan]-1,3-oxathiolane-2-thione

Conditions	Yield
With lithium bromide In dichloromethane for 8h; Inert atmosphere; Reflux; regioselective reaction;	67%

diethylene glycol diglycidyl ether (4206-61-5) + Cyclohexyl isocyanate (3173-53-3) → 5-(9-oxiran-2,5,8-trioxanonan-5-yl)-3-cyclohexyloxazolidin-2-one

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: Cyclohexyl isocyanate In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	65%

Propyl isocyanate (110-78-1) + diethylene glycol diglycidyl ether (4206-61-5) → 5-(9-oxiran-2,5,8-trioxanonan-5-yl)-3-propyloxazolidin-2-one

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: Propyl isocyanate In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	60%

carbon disulfide (75-15-0) + Propyl isocyanate (110-78-1) + diethylene glycol diglycidyl ether (4206-61-5) → 5-(6-oxathiolan-2-thione-2,5,8-trioxanonan-5-yl)-3-propyloxazolidin-2-one

Conditions	Yield
Stage #1: diethylene glycol diglycidyl ether With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: Propyl isocyanate In tetrahydrofuran Inert atmosphere; Reflux; Stage #3: carbon disulfide In tetrahydrofuran at 20℃; for 15h; Inert atmosphere;	60%

Tetrahydrofurfuryl alcohol (97-99-4) + diethylene glycol diglycidyl ether (4206-61-5) → 2-(tetrahydrofurfuryl)-12-hydroxy-13-crown-4

Conditions	Yield
With lithium In tert-butyl alcohol at 60℃; for 30h;	59%

diethylene glycol diglycidyl ether (4206-61-5) → 9,13-dihydroxy-1,4,7-trioxa-11-thiacyclotetradecane (100228-56-6)

Conditions	Yield
With sodium hydrogensulfide In water at 60℃; for 0.5h;	58%

diethylene glycol diglycidyl ether (4206-61-5) + 1,11-dimercapto-3,6,9-trioxaundecane (2781-02-4) → C18H36O8S2

Conditions	Yield
With potassium carbonate In methanol at 65℃; for 3h;	51.8%

diethylene glycol diglycidyl ether (4206-61-5) + SEC-BUTYLAMINE (33966-50-6) → 11-sec-Butyl-1,4,7-trioxa-11-aza-cyclotetradecane-9,13-diol (90655-84-8)

Conditions	Yield
In methanol at 55℃; for 7h;	49%

diethylene glycol diglycidyl ether (4206-61-5) + aniline (62-53-3) → 11-Phenyl-1,4,7-trioxa-11-aza-cyclotetradecane-9,13-diol (90655-87-1)

Conditions	Yield
In methanol for 100h; Ambient temperature;	48%

diethylene glycol diglycidyl ether (4206-61-5) + carbon dioxide (124-38-9) → C12H18O9 (116146-29-3)

Conditions	Yield
With choline iodide In ethanol at 85℃; under 7500.75 Torr; for 6h; Solvent;	46%

2,3-dichlorotetrahydrofuran (3511-19-1) + diethylene glycol diglycidyl ether (4206-61-5) → 1,15-di(3-chloro-2-tetrahydrofuryl)-3,13-dichloro-1,5,8,11,15-pentaoxapentadecane (137675-80-0)

Conditions	Yield
With zinc(II) chloride In tetrachloromethane at 40℃; for 1h;	45.5%

diethylene glycol diglycidyl ether (4206-61-5) + 1-aminodecane (2016-57-1) → 11-Decyl-9,13-dihydroxy-1,4,7-trioxa-11-azacyclotetradecane (90655-86-0)

Conditions	Yield
In methanol for 50h; Ambient temperature;	43%

diethylene glycol diglycidyl ether (4206-61-5) + bis(2-mercaptoethyl)ether (2150-02-9) → C14H28O6S2

Conditions	Yield
With sodium carbonate In methanol at 65℃; for 3h;	42%

diethylene glycol diglycidyl ether (4206-61-5) + diaza[12]crown-4 (294-92-8) → 3,13,23,33-tetrahydroxy-5,8,11,18,25,28,31,38,43,48-decaoxa-1,15,21,35-tetraazatricyclo<33.33.5.51,35>pentacontane (119017-30-0) + meso-3,13-dihydroxy-5,8,11,18,23-pentaoxa-1,15-diazabicyclo<13.5.5>pentacosane (173396-16-2)

Conditions	Yield
In tetrahydrofuran; ethanol for 10h; Heating;	A 6% B 41%
In tetrahydrofuran; ethanol for 10h; Heating;

diethylene glycol diglycidyl ether (4206-61-5) + ethylamine (75-04-7) → 11-Ethyl-1,4,7-trioxa-11-aza-cyclotetradecane-9,13-diol (90655-79-1)

Conditions	Yield
In methanol; water for 50h; Ambient temperature;	38%

Upstream product

• 106-89-8 epichlorohydrin 
• 111-46-6 diethylene glycol 
• 57947-82-7 bis(allyloxy)diethylene glycol 

Downstream Products

• 90655-87-1 11-Phenyl-1,4,7-trioxa-11-aza-cyclotetradecane-9,13-diol 
• 156366-10-8 1-(2-{2-[2-Hydroxy-3-(4-vinyl-phenoxy)-propoxy]-ethoxy}-ethoxy)-3-(4-vinyl-phenoxy)-propan-2-ol 

Relevant articles and documents

Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides

The title thiacrown ethers were prepared in a one-step procedure to give a series of unique macrocycles possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson's birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared for the first time.

Application of HPLC for the screening of separation of new macrocyclic systems

The efficient synthesis of new macrocyclic systems via nucleophilic ring opening reaction of epoxides by thiols was described. Initially new macrocyclic compounds were obtained as a mixture of diastereomers. Preparative thin layer chromatography was applied to separate meso and pairs of enantiomer. The identification of products using a chiral HPLC column and mass spectroscopy was utilized.

Solvent-free synthesis of dihydroxy dithiacrown ethers

The solvent-free reaction of oligoethylene glycol diglycidyl ethers with dimercaptoethane in the presence of benzyltrimethylammonium hydroxide (Triton B) gave, via regiospecific epoxide opening reactions, dihydroxy dithiacrown ethers in excellent yields and in short reaction times.