2461-15-6

Basic information

• Product Name: 2-Ethylhexyl glycidyl ether
• Synonyms: (((2-ethylhexyl)oxy)methyl)-oxiran;(((2-Ethylhexyl)oxy)methyl)oxirane;[(2-Ethylhexyl)methyl]oxirane;[[(2-ethylhexyl)oxy]methyl]-oxiran;[[(2-ethylhexyl)oxy]methyl]-Oxirane;1,2-epoxy-3-((2-ethylhexyl)oxy)-propan;2-ethvlhexvlglvcidvlether;2-Ethylhexyl 2-oxiranylmethyl ether
• CAS NO: 2461-15-6
• Molecular Formula: C₁₁H₂₂O₂
• Molecular Weight: 186.29
• EINECS: 219-553-6
• Product Categories: Oxiranes;Simple 3-Membered Ring Compounds;Epoxide Monomers;Monomers;Polymer Science
• Mol File: 2461-15-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 118-120°C
• Flash Point: 206°F
• Appearance: colourless liquid
• Density: 0.891
• Vapor Pressure: 0.0209mmHg at 25°C
• Refractive Index: 1.434
• Water Solubility: <0.1 g/100 mL at 19℃
• Stability: Stable. Combustible. Incompatible with strong oxidising agents, acids, bases.
• CAS DataBase Reference: 2-Ethylhexyl glycidyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylhexyl glycidyl ether(2461-15-6)
• EPA Substance Registry System: 2-Ethylhexyl glycidyl ether(2461-15-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: TZ3300000
• Hazardous Substances Data: 2461-15-6(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 2461-15-6 differently. You can refer to the following data:
1. It constitutes a reactive diluent and may be used as a relatively nonvolatile chloride-scavenging agent and stabilizer for vinyl resins and rubber.
2. 2-Ethylhexyl glycidyl ether is a used as a commercial reactive diluent. 2-Ethylhexyl glycidyl ether is also known to induce sister-chromatid exchanges in Chinese hamster cells.

Production Methods

2-Ethylhexyl glycidyl ether is made by condensation of 2-ethylhexanol with epichlorohydrin followed by dehydrochlorination with caustic to form the epoxy ring.

General Description

Clear colorless liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Ethylhexyl glycidyl ether is incompatible with acids, bases and oxidizing agents.

Fire Hazard

2-Ethylhexyl glycidyl ether is combustible.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C11H22O2/c1-3-5-6-10(4-2)7-12-8-11-9-13-11/h10-11H,3-9H2,1-2H3

Synthetic route

1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol (37961-18-5) → 2-ethyl-hexyl glycidyl ether (2461-15-6)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20 - 25℃; for 18h;

2-Ethylhexyl alcohol (104-76-7) + epichlorohydrin (106-89-8) → 2-ethyl-hexyl glycidyl ether (2461-15-6) + 1,3-di(2-ethylhexyloxy)-2-propylglycidyl ether + 3-chloroprop-2-enylglycidyl ether

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol With tetrabutylammomium bromide; sodium hydroxide at -40℃; for 0.5h; Inert atmosphere; Stage #2: epichlorohydrin at 80℃; for 12h; Reagent/catalyst; Temperature;

2-Ethylhexyl alcohol (104-76-7) + epichlorohydrin (106-89-8) → 2-ethyl-hexyl glycidyl ether (2461-15-6)

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol With tetrabutylammomium bromide; sodium hydroxide at -40℃; for 0.5h; Inert atmosphere; Stage #2: epichlorohydrin at 40℃; for 12h; Reagent/catalyst; Temperature;
Stage #1: 2-Ethylhexyl alcohol; epichlorohydrin With sulfuric acid; (3-chloro-2-hydroxypropyl)-2-ethylhexyl ether at 80 - 100℃; for 4h; Stage #2: With sodium hydroxide at 50℃; Stage #3: With sodium chloride; sodium hydroxide In water at 85 - 95℃; for 6h;	752.8 g

2-Ethylhexyl alcohol (104-76-7) + epichlorohydrin (106-89-8) → 2-ethyl-hexyl glycidyl ether (2461-15-6) + 1,3-di(2-ethylhexyloxy)-2-propylglycidyl ether

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol With tetrabutylammomium bromide; sodium hydroxide at -40℃; for 0.5h; Inert atmosphere; Stage #2: epichlorohydrin at 60℃; for 12h; Reagent/catalyst; Temperature;

2-Ethylhexyl alcohol (104-76-7) + epichlorohydrin (106-89-8) → 2-ethyl-hexyl glycidyl ether (2461-15-6) + 5,13-diethyl-7,11-dioxa-9-heptadecanol (59068-03-0)

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol With tetrabutylammomium bromide; sodium hydroxide at -40℃; for 0.5h; Inert atmosphere; Stage #2: epichlorohydrin at 40℃; for 12h; Reagent/catalyst; Temperature;

2-ethyl-hexyl glycidyl ether (2461-15-6) → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With formic acid; water; sodium hydroxide In Triethylene glycol dimethyl ether at 120℃; for 12h; Reagent/catalyst; Solvent;	98.5%
Stage #1: 2-ethyl-hexyl glycidyl ether With boron trifluoride diethyl etherate In acetone at 10 - 20℃; for 2.66667h; Stage #2: With methylamine In water; acetone at 10 - 20℃; for 0.166667h; Stage #3: With formic acid In water at 50 - 55℃; for 3h; Temperature; Reagent/catalyst;	89.1%
Stage #1: 2-ethyl-hexyl glycidyl ether With formic acid; sulfuric acid at 80 - 100℃; Stage #2: With methanol at 60℃; Stage #3: With water; sodium hydroxide Product distribution / selectivity;	78.1%

2-ethyl-hexyl glycidyl ether (2461-15-6) + 3-(2-ethylhexoxy)propylamine (5397-31-9) → C33H69NO5

Conditions	Yield
at 60 - 120℃; for 10.67h;	98%

2-ethyl-hexyl glycidyl ether (2461-15-6) → 2-(4-ethyl-2-oxaoctyl)thiirane (71242-04-1)

Conditions	Yield
With thiourea In methanol for 48h; Ambient temperature;	97.4%

2-ethyl-hexyl glycidyl ether (2461-15-6) + carbon dioxide (124-38-9) → 4-(((2-ethylhexyl)oxy)methyl)-1,3-dioxolan-2-one

Conditions	Yield
With tetrabutylammomium bromide at 110℃; under 7500.75 Torr; for 3h;	91%
With (2-aminoethyl)(4-(bis(2,6-dimethoxyphenyl)methylene)-3,5-dimethoxycyclohexa-2,5-dien-1-yl)diphenylphosphonium trifluoromethanesulfonate; sodium iodide In chlorobenzene at 100℃; under 760.051 Torr; for 12h; Schlenk technique;	91%
With C24H12N2O10(4-)*2Cu(2+); tetrabutylammomium bromide at 20℃; under 760.051 Torr; for 48h; Schlenk technique;	6%

2-Ethylhexylamine (104-75-6) + 2-ethyl-hexyl glycidyl ether (2461-15-6) → poly(2-ethylhexylamine-co-2-ethylhexyl glycidyl ether)

Conditions	Yield
at 60 - 120℃; for 10.6667h;	90%

2-ethyl-hexyl glycidyl ether (2461-15-6) + carbon monoxide (201230-82-2) + 2-hydroxybromobenzene (95-56-7) → 3-(((2-ethylhexyl)oxy)methyl)-2H-benzo[e][1,4]dioxepin-5(3H)-one (1556674-22-6)

Conditions	Yield
With potassium phosphate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In N,N-dimethyl-formamide at 100℃; under 3750.38 Torr; for 16h; Autoclave;	88%

3-(dodecyloxy)-1-propylamine (7617-74-5) + 2-ethyl-hexyl glycidyl ether (2461-15-6) → poly(2-ethylhexyl glycidyl ether-co-3-(dodecyloxy)-1-propylamine)

Conditions	Yield
at 60 - 120℃; for 10.6667h;	85%

2-ethyl-hexyl glycidyl ether (2461-15-6) + 2-Ethylhexyl alcohol (104-76-7) → 5,13-diethyl-7,11-dioxa-9-heptadecanol (59068-03-0)

Conditions	Yield
sulfated zirconium oxide at 150℃; Inert atmosphere;	83.2%
With sodium hydride for 48h; Ambient temperature;	61%
With tetrabutylammomium bromide; sodium hydroxide at 60℃; Cooling with ice;

carbon disulfide (75-15-0) + 2-ethyl-hexyl glycidyl ether (2461-15-6) → 4-(4-ethyl-2-oxaoctyl)-1,3-dithiolane-2-thione

Conditions	Yield
With potassium hydroxide In methanol for 96h; Ambient temperature;	82%

2-ethyl-hexyl glycidyl ether (2461-15-6) + i-Amyl alcohol (123-51-3) → 11-ethyl-2-methyl-5,9-dioxa-7-pentadecanol (93314-60-4)

Conditions	Yield
With sodium hydride for 48h; Ambient temperature;	79%

2-ethyl-hexyl glycidyl ether (2461-15-6) + 4-(4,6-diphenyl-pyrimidin-2-yl)-benzene-1,3-diol (2915-23-3) → C33H38N2O4 (163263-83-0)

Conditions	Yield
With ethyltriphenylphosphonium bromide at 150℃; for 0.5h;	71.7%

2-ethyl-hexyl glycidyl ether (2461-15-6) + (+/-)-2-methyl-1-butanol (137-32-6) → 11-ethyl-3-methyl-5,9-dioxa-7-pentadecanol (174719-45-0)

Conditions	Yield
With sodium hydride for 48h; Ambient temperature;	69%

2-ethyl-hexyl glycidyl ether (2461-15-6) + C9H9N*HO3S → sulfuric acid mono-[2-(3,4-dihydro-isoquinolin-2-yl)-1-(2-ethyl-hexyloxymethy)-ethyl] ester

Conditions	Yield
at 75 - 80℃; for 72h; Product distribution / selectivity;	68%

7,8-benzoquinoline (230-27-3) + 2-ethyl-hexyl glycidyl ether (2461-15-6) → 1-(benzo[h]quinolin-10-yl)-3-((2-ethylhexyl)oxy)-2-propanol

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; palladium diacetate; acetic acid at 25℃; for 24h; Inert atmosphere;	58%

3,4-dihydroisoquinoline (3230-65-7) + 2-ethyl-hexyl glycidyl ether (2461-15-6) → sulfuric acid mono-[2-(3,4-dihydro-isoquinolin-2-yl)-1-(2-ethyl-hexyloxymethy)-ethyl] ester

Conditions	Yield
In acetonitrile at 80℃; for 72h; Product distribution / selectivity;	55%

2-ethyl-hexyl glycidyl ether (2461-15-6) + 3,4,9,10-perylenetetracarboxylic diimide bis(tetrabutylammonium) salt → C46H54N2O8

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere;	50%

2-ethyl-hexyl glycidyl ether (2461-15-6) → 9-ethyl-5-(5-methyl-2-oxa-1-hexyl)-4,7-dioxa-1-tridecanesulfonic acid sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: 98 percent / sodium hydride / dimethylformamide / 3 h View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 12-ethyl-8-(5-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecanesulfonic acid sodium salt

Conditions	Yield
Multi-step reaction with 4 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: sodium hydride / acetonitrile / 0.5 h / Heating; before reflux 1 h room temperature 3: 1M HCl / 2 h / Heating 4: 100 percent / sodium hydride / dimethylformamide / 1 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: 89 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 3: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature 4: 100 percent / sodium hydride / dimethylformamide / 1 h / 60 °C View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 6-ethyl-4-oxadecane-1,2-dithiol (174719-33-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97.4 percent / thiourea / methanol / 48 h / Ambient temperature 2: 37 percent / sodium hydrosulfide, hydrogen sulfide / ethanol / 3 h View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 8-ethyl-4-(4-methyl-2-oxa-1-hexyl)-3,6-dioxa-1-dodecanol (174719-47-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / sodium hydride / 48 h / Ambient temperature 2: 93 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 3: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 8-ethyl-4-(5-methyl-2-oxa-1-hexyl)-3,6-dioxa-1-dodecanol (174719-42-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: sodium hydride / acetonitrile / 0.5 h / Heating; before reflux 1 h room temperature 3: 1M HCl / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: 89 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 3: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 11-ethyl-2-methyl-5,9-dioxa-7-pentadecanone

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: PDC / dimethylformamide View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 11-ethyl-3-methyl-5,9-dioxa-7-pentadecanone

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / sodium hydride / 48 h / Ambient temperature 2: PDC / dimethylformamide View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 11-ethyl-7-(5-methyl-2-oxa-1-hexyl)-3,6,9-trioxa-1-pentadecanol (174719-44-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: sodium hydride / acetonitrile / 0.5 h / Heating; before reflux 1 h room temperature 3: 1M HCl / 2 h / Heating 4: 78.7 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 5: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature View Scheme
Multi-step reaction with 5 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: 89 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 3: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature 4: 78.7 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 5: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 11-ethyl-7-(4-methyl-2-oxa-1-hexyl)-3,6,9-trioxa-1-pentadecanol (174719-49-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: 69 percent / sodium hydride / 48 h / Ambient temperature 2: 93 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 3: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature 4: 17 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 5: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 9-ethyl-5-(4-methyl-2-oxa-1-hexyl)-4,7-dioxa-1-tridecene (174719-46-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / sodium hydride / 48 h / Ambient temperature 2: 93 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 9-ethyl-5-(5-methyl-2-oxa-1-hexyl)-4,7-dioxa-1-tridecene (174719-41-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: 89 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 12-ethyl-8-(5-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecene (174719-43-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: sodium hydride / acetonitrile / 0.5 h / Heating; before reflux 1 h room temperature 3: 1M HCl / 2 h / Heating 4: 78.7 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: 79 percent / sodium hydride / 48 h / Ambient temperature 2: 89 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 3: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature 4: 78.7 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → 12-ethyl-8-(4-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecene (174719-48-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 69 percent / sodium hydride / 48 h / Ambient temperature 2: 93 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C 3: 1.) ozone, 2.) sodium borohydride / 1.) methanol, -78 deg C, 2.) methanol, to room temperature 4: 17 percent / sodium hydride / tetrahydrofuran / 22 h / 60 °C View Scheme

Upstream product

• 104-76-7 2-Ethylhexyl alcohol 
• 106-89-8 epichlorohydrin 
• 37961-18-5 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol 

Downstream Products

• 163263-83-0 C₃₃H₃₈N₂O₄ 
• 198225-43-3 N-[2-Hydroxy-3-(2-ethyl)hexanoxypropyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine 
• 1174337-27-9 5-(((2-ethylhexyl)oxy)methyl)-3-phenyloxazolidin-2-one 
• 70445-33-9 1-O-(2-ethylhexyl)glycerin 
• 59068-03-0 5,13-diethyl-7,11-dioxa-9-heptadecanol 

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