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Basic Information
CAS No.: 2461-15-6
Name: 2-Ethylhexyl glycidyl ether
Article Data: 5
Molecular Structure:
Molecular Structure of 2461-15-6 (2-Ethylhexyl glycidyl ether)
Formula: C11H22O2
Molecular Weight: 186.294
Synonyms: Oxirane,[[(2-ethylhexyl)oxy]methyl]- (9CI);Propane, 1,2-epoxy-3-[(2-ethylhexyl)oxy]-(6CI,7CI,8CI);1-(2-Ethylhexyloxy)-2,3-epoxypropane;Oxirane,2-[[(2-ethylhexyl)oxy]methyl]-;Adeka Glycilol ED 518;Adeka Glycilol ED 518S;Denacol EX 12;Denacol EX121;ED 518;Epiol EH;Epodil 746;Epodil 747;Glycidyl 2-ethylhexyl ether;Grilonit 1807-41;Heloxy 116;Heloxy MK 116;JX 014;Laproxid 301;NSC 252154;[[(2-Ethylhexyl)oxy]methyl]oxirane;
EINECS: 219-553-6
Density: 0.913 g/cm3
Boiling Point: 259.452 °C at 760 mmHg
Flash Point: 96.667 °C
Solubility: <0.1 g/100 mL at 19 °C in water
Appearance: colourless liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
PSA: 21.76000
LogP: 2.61820
Synthetic route
37961-18-5

1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol

2461-15-6

2-ethyl-hexyl glycidyl ether

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20 - 25℃; for 18h;
104-76-7

2-Ethylhexyl alcohol

106-89-8

epichlorohydrin

A

2461-15-6

2-ethyl-hexyl glycidyl ether

B

1,3-di(2-ethylhexyloxy)-2-propylglycidyl ether

C

3-chloroprop-2-enylglycidyl ether

Conditions
ConditionsYield
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;
104-76-7

2-Ethylhexyl alcohol

106-89-8

epichlorohydrin

2461-15-6

2-ethyl-hexyl glycidyl ether

Conditions
ConditionsYield
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
104-76-7

2-Ethylhexyl alcohol

106-89-8

epichlorohydrin

A

2461-15-6

2-ethyl-hexyl glycidyl ether

B

1,3-di(2-ethylhexyloxy)-2-propylglycidyl ether

Conditions
ConditionsYield
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;
104-76-7

2-Ethylhexyl alcohol

106-89-8

epichlorohydrin

A

2461-15-6

2-ethyl-hexyl glycidyl ether

B

59068-03-0

5,13-diethyl-7,11-dioxa-9-heptadecanol

Conditions
ConditionsYield
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;
2461-15-6

2-ethyl-hexyl glycidyl ether

70445-33-9

1-O-(2-ethylhexyl)glycerin

Conditions
ConditionsYield
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%
2461-15-6

2-ethyl-hexyl glycidyl ether

5397-31-9

3-(2-ethylhexoxy)propylamine

C33H69NO5

Conditions
ConditionsYield
at 60 - 120℃; for 10.67h;98%
2461-15-6

2-ethyl-hexyl glycidyl ether

71242-04-1

2-(4-ethyl-2-oxaoctyl)thiirane

Conditions
ConditionsYield
With thiourea In methanol for 48h; Ambient temperature;97.4%
2461-15-6

2-ethyl-hexyl glycidyl ether

124-38-9

carbon dioxide

4-(((2-ethylhexyl)oxy)methyl)-1,3-dioxolan-2-one

Conditions
ConditionsYield
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%
104-75-6

2-Ethylhexylamine

2461-15-6

2-ethyl-hexyl glycidyl ether

poly(2-ethylhexylamine-co-2-ethylhexyl glycidyl ether)

poly(2-ethylhexylamine-co-2-ethylhexyl glycidyl ether)

Conditions
ConditionsYield
at 60 - 120℃; for 10.6667h;90%
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    2-Ethylhexyl glycidyl ether Basic information Product Name: 2-Ethylhexyl glycidyl ether Synonyms: glycidyl2-ethylhexylether;Oxirane,[[(2-ethylhexyl)oxy]methyl]-;Propane, 1,2-epoxy-3-[(2-ethylhexyl)oxy]-;EHGE;(2-ETHYLHEXYLOXY)-2,3-EPOXYPROPANE;

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2-Ethylhexyl glycidyl ether, with the CAS registry number 2461-15-6, is also known as Oxirane,2-[[(2-ethylhexyl)oxy]methyl]-. It belongs to the product categories of Oxiranes; Simple 3-Membered Ring Compounds; Epoxide Monomers; Monomers; Polymer Science. Its EINECS number is 219-553-6. This chemical's molecular formula is C11H22O2 and molecular weight is 186.29. What's more, its systematic name is 2-{[(2-Ethylhexyl)oxy]methyl}oxirane. Its classification codes are: (1)Mutation data; (2)TSCA Flag T [Subject to the Section 4 test rule under TSCA]. This chemical should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from light. It is used as active diluents to reduce resin viscosity and improve the flexibility. It is also used to pour electric products in filament winding so as to increase mechanical properties.

Physical properties of 2-Ethylhexyl glycidyl ether are: (1)ACD/LogP: 3.259; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.26; (4)ACD/LogD (pH 7.4): 3.26; (5)ACD/BCF (pH 5.5): 176.62; (6)ACD/BCF (pH 7.4): 176.62; (7)ACD/KOC (pH 5.5): 1412.64; (8)ACD/KOC (pH 7.4): 1412.64; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 21.76 Å2; (13)Index of Refraction: 1.445; (14)Molar Refractivity: 54.289 cm3; (15)Molar Volume: 204.141 cm3; (16)Polarizability: 21.522×10-24cm3; (17)Surface Tension: 31.69 dyne/cm; (18)Density: 0.913 g/cm3; (19)Flash Point: 96.667 °C; (20)Enthalpy of Vaporization: 47.703 kJ/mol; (21)Boiling Point: 259.452 °C at 760 mmHg; (22)Vapour Pressure: 0.021 mmHg at 25°C.

Uses of 2-Ethylhexyl glycidyl ether: it can be used to produce 2-(4-ethyl-2-oxaoctyl)thiirane at the ambient temperature. It will need reagent thiourea and solvent methanol with the reaction time of 48 hours. The yield is about 97.4%.

2-Ethylhexyl glycidyl ether can be used to produce 2-(4-ethyl-2-oxaoctyl)thiirane at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O(CC(CCCC)CC)CC1OC1
(2)Std. InChI: InChI=1S/C11H22O2/c1-3-5-6-10(4-2)7-12-8-11-9-13-11/h10-11H,3-9H2,1-2H3
(3)Std. InChIKey: BBBUAWSVILPJLL-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 7800mg/kg (7800mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2A, Pg. 2210, 1981.

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