112-49-2

Basic information

• Product Name: TRIETHYLENE GLYCOL DIMETHYL ETHER
• Synonyms: (CH3O(CH2)2OCH2)2;Ansul Ether 161;ansulether161;Dimethyl ether of triethylene glycol;Ethane, 1,2-bis(2-methoxyethoxy)-;ethane,1,2-bis(2-methoxyethoxy)-;Glyme-3;glyme4
• CAS NO: 112-49-2
• Molecular Formula: C₈H₁₈O₄
• Molecular Weight: 178.23
• EINECS: 203-977-3
• Product Categories: Aliphatics;Isotope Labelled Compounds;Building Blocks;C2 to C8;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds;Functional Materials;Plasticizer;Polyalcohol Ethers, Esters (Plasticizer)
• Mol File: 112-49-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: −45 °C(lit.)
• Boiling Point: 216 °C(lit.)
• Flash Point: 231 °F
• Appearance: APHA: ≤20/Liquid
• Density: 0.986 g/mL at 25 °C(lit.)
• Vapor Density: >4.7 (vs air)
• Vapor Pressure: 0.539mmHg at 25°C
• Refractive Index: n20/D 1.423(lit.)
• Storage Temp.: Refrigerator
• Solubility: >1000g/l soluble
• Explosive Limit: 0.7%(V)
• Water Solubility: Soluble
• Sensitive: Hygroscopic
• Merck: 14,9692
• BRN: 1700630
• CAS DataBase Reference: TRIETHYLENE GLYCOL DIMETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: TRIETHYLENE GLYCOL DIMETHYL ETHER(112-49-2)
• EPA Substance Registry System: TRIETHYLENE GLYCOL DIMETHYL ETHER(112-49-2)

Safety Data

• Hazard Codes: T
• Statements: 61-19-62
• Safety Statements: 53-45
• WGK Germany: 1
• RTECS: XF0665000
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 112-49-2(Hazardous Substances Data)

Usage

Chemical Properties

Water-white liquid; mild ether odor. D 0.9862 (20/20C), refr index 1.4233 (20C), flash p 232F (111C), bp 216.0C (760mmHg), 153.6C (100 mm Hg), fp ?46C. Completely soluble in water and hydrocarbons at 20C. May contain peroxides. Combustible.

Uses

Different sources of media describe the Uses of 112-49-2 differently. You can refer to the following data:
1. Triethylene glycol dimethyl ether is used as a solvent for gases and coupling immiscible liquid. It is also used to prepare perfluoro-triethyleneglycoldimethylether.
2. Triethylene glycol dimethyl ether may be used as an analytical standard for the quantification of the analyte in water samples using in vitro bioassays and chemical screening technique.
3. Labelled Triglyme. It is used as a solvent.

Definition

ChEBI: A polyether that consists of dodecane in which the carbon atoms at positions 2, 5, 8 and 11 are replaced by oxygen atoms.

Reactivity Profile

TRIETHYLENE GLYCOL DIMETHYL ETHER forms explosive peroxides on prolonged exposure to air. Its decomposition products may be sensitive to shock. The bulk chemical is stable for 2 weeks at temperatures up to 140° F when protected from light. TRIETHYLENE GLYCOL DIMETHYL ETHER is incompatible with strong oxidizers. TRIETHYLENE GLYCOL DIMETHYL ETHER is also incompatible with strong acids. TRIETHYLENE GLYCOL DIMETHYL ETHER may react with peroxides, oxygen, nitric acid and sulfuric acid. .

Flammability and Explosibility

Nonflammable

Purification Methods

Reflux it with, and distil it from sodium hydride or LiAlH4. [Beilstein 1 IV 2401.]

InChI:InChI=1/C8H18O4/c1-8(11-6-4-9-2)12-7-5-10-3/h8H,4-7H2,1-3H3

Synthetic route

(2,5-dioxahexylsulfonyl)benzene → Triethylene glycol dimethyl ether (112-49-2)

Conditions	Yield
With sodium amalgam In benzene Heating;	79%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 1,2-dimethoxyethane (110-71-4) + Triethylene glycol dimethyl ether (112-49-2) + 2-methoxy-ethanol (109-86-4) + diethylene glycol dimethyl ether (111-96-6)

Conditions	Yield
5%-palladium/activated carbon; nickel at 220℃; under 2250.23 Torr; for 10h;	A 75% B 2% C 10% D 11%

dimethyl sulfate (77-78-1) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethylene glucol monomethyl ether (112-35-6) + Triethylene glycol dimethyl ether (112-49-2)

Conditions	Yield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydroxide at 55 - 60℃; for 0.166667h; Stage #2: dimethyl sulfate at 55 - 60℃; for 6h;	A 33% B n/a

1,1,2,2-tetrakis-(2-methoxy-ethoxy)-ethane (86220-16-8) → Triethylene glycol dimethyl ether (112-49-2)

Conditions	Yield
With nickel at 215 - 270℃; Hydrogenation.unter Druck;

methyl iodide (74-88-4) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → Triethylene glycol dimethyl ether (112-49-2)

Conditions	Yield
(i) TlOEt, benzene, (ii) /BRN= 969135/, MeCN; Multistep reaction;
With thallium (I) ethoxide 1) MeCN, r.t., 2) MeCN, 20 deg C, 14 h; Yield given. Multistep reaction;

C8H18O4*C3H9N*H(1+) → Triethylene glycol dimethyl ether (112-49-2) + trimethylammonium (145384-53-8)

Conditions	Yield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;

C8H18O4*C6H13N*H(1+) → cyclohexyl-ammonium cation (29384-28-9) + Triethylene glycol dimethyl ether (112-49-2)

Conditions	Yield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;

C8H18O4*C5H5N*H(1+) → pyridin-1-ium (16969-45-2) + Triethylene glycol dimethyl ether (112-49-2)

Conditions	Yield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;

C8H18O4*C4H4N2*H(1+) → Triethylene glycol dimethyl ether (112-49-2) + 1,2-diazineH+ (17009-97-1)

Conditions	Yield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;

C8H18O4*C4H12N(1+) → Triethylene glycol dimethyl ether (112-49-2) + tetramethylammonium (51-92-3)

Conditions	Yield
Thermodynamic data; by a 1-ms pulse of 500-1000 eV;

dimethyl sulfate (77-78-1) + disodium triethylene glycolate → Triethylene glycol dimethyl ether (112-49-2)

triethylene glycol dimethyl ether and lithium picrate complex → Triethylene glycol dimethyl ether (112-49-2) + lithium picrate-RG7

Conditions	Yield
With RG7 In toluene at 25℃; Equilibrium constant;

triethylene glycol dimethyl ether and sodium picrate complex → Triethylene glycol dimethyl ether (112-49-2) + sodium picrate-RG7

Conditions	Yield
With RG7 In toluene at 25℃; Equilibrium constant; other resins;

15-crown-5 (33100-27-5) + methyl iodide (74-88-4) → Triethylene glycol dimethyl ether (112-49-2) + tetraethylene glycol methyl vinyl ether

Conditions	Yield
With tetrahydrofuran; potassium miror at 20℃; for 24h; Product distribution; Further Variations:; Solvents;

glycidyl n-butyl ether (2426-08-6) + 15-crown-5 (33100-27-5) + methyl iodide (74-88-4) → Triethylene glycol dimethyl ether (112-49-2) + Tetraethylene glycol dimethyl ether (143-24-8) + propylene glycol methyl n-butyl ether + tetraethylene glycol methyl vinyl ether

Conditions	Yield
Stage #1: 15-crown-5 With potassium In tetrahydrofuran at 25℃; for 0.416667h; Stage #2: glycidyl n-butyl ether In tetrahydrofuran Stage #3: methyl iodide In tetrahydrofuran Title compound not separated from byproducts;

oxirane (75-21-8) + Dimethyl ether (115-10-6) → 1,2-dimethoxyethane (110-71-4) + Triethylene glycol dimethyl ether (112-49-2) + diethylene glycol dimethyl ether (111-96-6) + Tetraethylene glycol dimethyl ether (143-24-8) + pentaglyme (1191-87-3)

Conditions	Yield
With boron trifluoride dimethyl etherate In polyethyleneglycol dimethyl ether at 50 - 80℃; under 6750.68 - 10501.1 Torr; for 0.0333333h; Product distribution / selectivity;	A 18.6 - 36.4 %Chromat. B 7.5 - 15.4 %Chromat. C 15.6 - 34.8 %Chromat. D 1.7 - 7.6 %Chromat. E 0 - 2.6 %Chromat.

Dimethyl ether (115-10-6) → Triethylene glycol dimethyl ether (112-49-2) + diethylene glycol dimethyl ether (111-96-6) + Tetraethylene glycol dimethyl ether (143-24-8)

Conditions	Yield
sulfuric acid In water at 100℃; for 16h; Product distribution / selectivity;
Amberlite IR 120 at 100℃; for 24h; Product distribution / selectivity;

Triethylene glycol dimethyl ether (112-49-2) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → C2F6NO4S2(1-)*C8H18O4*Li(1+)

Conditions	Yield
at 79.84℃; for 0.5h;	100%
for 24h;

Triethylene glycol dimethyl ether (112-49-2) + magnesium bis(trifluoromethane solfonyl)imide (133395-16-1) → Mg(2+)*2C2F6NO4S2(1-)*2C8H18O4

Conditions	Yield
at 100℃; Sealed tube;	100%

Triethylene glycol dimethyl ether (112-49-2) + manganese(II) bistriflimide hexahydrate → [manganese(II)(triglyme)] bistriflimide hexahydrate

Conditions	Yield
In acetonitrile at 20℃; for 1h;	99%

Triethylene glycol dimethyl ether (112-49-2) + Y(3+)*3CF3COCHCOCF3(1-)*H2O={Y(CF3COCHCOCF3)3(H2O)} → {((CF3COCHCOCF3)3Y)2(CH3OC2H4OC2H4OC2H4OCH3)}

Conditions	Yield
In hexane under N2: addn. of 1.50 mmol (Y(CF3COCHCOCF3)3(H2O))n to n-hexane; addn. of 1.50 mmol triglyme; stirring for 1 h; removing of solvent and H2O under vac.;; storing for several days; crystallization; elem. anal.;;	98%

Triethylene glycol dimethyl ether (112-49-2) + {Eu((CH3)3CCOCHCOC(CH3)3)3(H2O)} → {(Eu((CH3)3CCOCHCOC(CH3)3)3)2C8H18O4}

Conditions	Yield
In hexane under N2: dissolving 2 mmol (Eu(C(CH3)3COCHCOC(CH3)3)3(H2O)) in hexane; addn. of 2 mmol triglyme; stirring for 1 h;; removing of solvent in vac.; storing under vac. at 65°C for 1 h; cooling to room temperature; crystallization within 3 d; elem. anal.;;	97%

Triethylene glycol dimethyl ether (112-49-2) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → lithium triethylene glycol dimethyl ether bis(trifluoromethanesulfonyl)imide (1397679-83-2, 1446426-43-2)

Conditions	Yield
In dichloromethane for 72h; Inert atmosphere;	95%
In diethyl ether at 60℃; Inert atmosphere;
at 60℃; for 3h;

tetrahydrofuran (109-99-9) + Triethylene glycol dimethyl ether (112-49-2) + yttrium(III) trifluoroacetate trihydrate + sodium hydride (7646-69-7) + trifluoroacetic acid (76-05-1) → [Na(η4-triglyme)2][Y2(μ-η1:η1-trifluoroacetate)7(tetrahydrofuran)2]

Conditions	Yield
In tetrahydrofuran under Ar; soln. of NaH (0.62 mmol) and CF3COOH (0.65 mmol) in THF added dropwise to soln. of Y compd. (1.20 mmol) in THF, triglyme (1.21 mmol) added after 10 min, mixt. stirred at room temp. for 4 h; solvent removed, residue washed twice with n-hexane, dissolved in THF, soln. carefully layered with Et2O, system stored overnight, crystals isolated; elem. anal.;	93%
In tetrahydrofuran under Ar; soln. of NaH (1.46 mmol) and CF3COOH (1.40 mmol) in THF added dropwise to soln. of Y compd. (1.39 mmol) in THF, triglyme added after 10 min, mixt. stirred at room temp. for 4 h; solvent removed, residue washed twice with n-hexane, dissolved in THF, soln. carefully layered with Et2O, system stored overnight, crystals isolated; elem. anal.;	87%

ammonium iodide + copper(l) iodide (7681-65-4) + barium iodide dihydrate + Triethylene glycol dimethyl ether (112-49-2) + acetone (67-64-1) → [Ba(triglyme)2(acetone)2][Cu4I6]

Conditions	Yield
for 4h; Schlenk technique; Inert atmosphere;	91%

Triethylene glycol dimethyl ether (112-49-2) + {Tb((CH3)3CCOCHCOC(CH3)3)3(H2O)} → {(Tb((CH3)3CCOCHCOC(CH3)3)3)2C8H18O4}

Conditions	Yield
In hexane under N2: dissolving of 0.635 mmol (Tb(C(CH3)3COCHCOC(CH3)3)3(H2O)) in hexane; addn. of 0.635 mmol triglyme; stirring for 1 h;; removing of solvent in vac.; storing under vac. at 65°C for 1 h; cooling to room temperature; crystallization within 24 h; elem. anal.;;	90%

lanthanum(III) oxide + Triethylene glycol dimethyl ether (112-49-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) → La(hexafluoroacetylacetonate)3 * 2,5,8,11-tetraoxadodecane

Conditions	Yield
In benzene solvent removal; elem. anal.;	90%

Triethylene glycol dimethyl ether (112-49-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + barium carbonate → C44H82Ba2O20 + C18H34BaO9

Conditions	Yield
In hexane at 20℃; for 10h;	A 10% B 90%

Triethylene glycol dimethyl ether (112-49-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + water (7732-18-5) + barium carbonate → C18H22BaF12O9

Conditions	Yield
In ethanol at 20℃; for 3h;	90%

Triethylene glycol dimethyl ether (112-49-2) → bis(difluorophosphoryl)(2,5,8,11-tetraoxadodecane)dilithium

Conditions	Yield
With difluorophosphinic acid lithium salt at 20℃; for 3h;	88.4%

Triethylene glycol dimethyl ether (112-49-2) + yttrium(III) hydroxide hydrate + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) → [(2,5,8,11-tetraoxadodecane)tris(1,1,1,5,5,5-hexafluoroacetylacetonato)yttrium(III)] dihydrate

Conditions	Yield
In hexane to a suspn. of Y compd. (excess) added triglyme, after 10 min Hhfa addedwith vidorous stirring, refluxed for 1 h; hot filtered, concd., ppt. filtered, dried (vac.); elem. anal., TGA;	88%

sodium molybdate dihydrate (7631-95-0) + Triethylene glycol dimethyl ether (112-49-2) + hydrogen bromide (10035-10-6, 12258-64-9) → MoO2Br2(H2O)2*(C8H18O4)

Conditions	Yield
In diethyl ether; hydrogen bromide aq. HBr; soln. of Na2MoO4 in 47% HBr extd. in diethyl ether (3x50 ml), soln. treated with polyether; soln. stored overnight at -40°C, crystd., washed (Et2O), dried inair at room temp., elem. anal.;	85%

Triethylene glycol dimethyl ether (112-49-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + silver(l) oxide (20667-12-3) → C10H2AgF12O4(1-)*C16H36AgO8(1+)

Conditions	Yield
In dichloromethane for 1h; Reflux;	82%

tetrahydrofuran (109-99-9) + samarium (7440-19-9) + Triethylene glycol dimethyl ether (112-49-2) + 1,2-Diiodoethane (624-73-7) → cis-[SmI2(triglyme)(tetrahydrofuran)] (710945-89-4)

Conditions	Yield
In tetrahydrofuran Sonication; under Ar; C2H4I2 and THF added at ambient temp. to centrifuge tube contg. Sm chips (molar ratio 1:1.2); sonicated at 50°C for 3 h; centrifuged; triglyme (1 equiv.) added slowly to soln.; crystd. for 24 h; soln. removed; crystals washed with cold hexane; dried under vac.;	81%

Triethylene glycol dimethyl ether (112-49-2) + hypochlorous acid 4-methylbenzene sulfonic anhydride (103057-51-8) → [2-[2-(2-methoxyethoxy)ethoxy]ethoxy] p-toluenesulfonate

Conditions	Yield
Stage #1: Triethylene glycol dimethyl ether With sodium hydroxide In tetrahydrofuran; water for 2h; Cooling with ice; Stage #2: hypochlorous acid 4-methylbenzene sulfonic anhydride In tetrahydrofuran; water at 20℃;	81%

Triethylene glycol dimethyl ether (112-49-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + water (7732-18-5) + cobalt(II) hydroxide → [Co(1,1,1,5,5,5-hexafluoro-2,4-pentadionate(-H))2(H2O)2]*(2,5,8,11-tetraoxadodecane)

Conditions	Yield
In dichloromethane stoich. mixt. refluxed at 40°C for 2 h; filtered, evapd., treated with hexane, elem. anal.;	80%

Triethylene glycol dimethyl ether (112-49-2) + C52H62CaO4Si2 → C48H56CaO5Si2 (1562239-40-0)

Conditions	Yield
In tetrahydrofuran; pentane at -30℃; for 1h; Inert atmosphere;	80%

1,4-dioxane-2,6-dione (4480-83-5) + Triethylene glycol dimethyl ether (112-49-2) → {2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxycarbonylmethoxy}-acetic acid

Conditions	Yield
With stannous octoate In toluene Reflux; Inert atmosphere;	79.5%

Triethylene glycol dimethyl ether (112-49-2) + [Y(iPrOH)4]I3 + water (7732-18-5) → [Y2(μ-OH)2(H2O)2(iPrOH)2(η4-triglyme)2]I4

Conditions	Yield
In toluene Ar, toluene soln. of ligand and H2O soln. added to suspn. of Y compd., pptd. stirred at room temp. for 6 h; ppt. filtered off, washed (hexane), recrystd. (hot 2-propanol), elem. anal.;	77%

Triethylene glycol dimethyl ether (112-49-2) + bis(allyl)calcium (35815-10-2) → Ca(η3-C3H5)2(triglyme-κ4) (1187448-60-7)

Conditions	Yield
In tetrahydrofuran	77%

Triethylene glycol dimethyl ether (112-49-2) + bis(diphenylthiophosphinoyl)amine (6588-07-4) → C24H20NP2S2(1-)*C8H18O4*Na(1+)

Conditions	Yield
With sodium hydroxide In methanol; water for 0.5h; Addition;	75%

Triethylene glycol dimethyl ether (112-49-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + barium carbonate → C44H58Ba2F24O20

Conditions	Yield
In hexane at 50℃; for 3h;	75%

Triethylene glycol dimethyl ether (112-49-2) + bis(thf) calcocene (60173-07-1) → (η3-triglyme)CaCp2 (1272031-20-5)

Conditions	Yield
In tetrahydrofuran at 20℃; Inert atmosphere;	74.4%

Triethylene glycol dimethyl ether (112-49-2) + tin(II) bromide → C8H18O4*2Sn(2+)*4Br(1-)

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	74%

Triethylene glycol dimethyl ether (112-49-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + silver(l) oxide (20667-12-3) → [Ag(1,1,1,5,5,5-hexafluoropentane-2,4-dionate)(triglyme)] (215360-08-0)

Conditions	Yield
In tetrahydrofuran byproducts: water; absence of air and moisture; stirring Ag2O with 2 equiv. diketone and 2 equiv. glyme for 30 min; filtration (Celite), solvent removal (vac.), dissoln. in PhMe, layering with hexane, crystn. (room temp., overnight; then -20°C, 3 h), collection (filtration); elem. anal.;	73%

Upstream product

• 77-78-1 dimethyl sulfate 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 115-10-6 Dimethyl ether 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 75-21-8 oxirane 
• 2426-08-6 glycidyl n-butyl ether 
• 33100-27-5 15-crown-5 
• 74-88-4 methyl iodide 
• 86220-16-8 1,1,2,2-tetrakis-(2-methoxy-ethoxy)-ethane 

Downstream Products

• 123-91-1 1,4-dioxane 
• 110-71-4 1,2-dimethoxyethane 
• 115-10-6 Dimethyl ether 
• 640723-20-2 fluorosulfonyl fluoride 
• 116-15-4 perfluoropropylene 
• 74-90-8 hydrogen cyanide 
• 460-19-5 ethanedinitrile 
• 558-25-8 methyl fluorosulfonate 
• 380-29-0 methyl-pentafluoroallyl ether 
• 7792-66-7 2,2,3,4,4-pentafluorobut-3-ene nitrile 
• 667-49-2 2,3,3-trifluoroacryloyl fluoride 
• 7446-09-5 sulfur dioxide 
• 7789-21-1 fluorosulphonic acid 
• 7783-61-1 silicon tetrafluoride 

Related news

The developmental toxicity of TRIETHYLENE GLYCOL DIMETHYL ETHER (cas 112-49-2) in mice☆08/24/2019

Triethylene glycol dimethyl ether (triEGdiME) is structurally related to several compounds which produce reproductive and developmental toxicity, including teratogenicity in laboratory animals. In the present study, triEGdiME (0, 250, 500, or 1000 mg/kg/day) was administered by gavage to timed-p...detailed

Conformational adaptation of TRIETHYLENE GLYCOL DIMETHYL ETHER (cas 112-49-2) in cation capture as studied by Raman spectroscopy08/23/2019

Measurements of Raman spectra of triethylene glycol dimethyl ether and its cation complexes were carried out. It was found by analyses of the spectra and normal vibration calculations that triethylene glycol dimethyl ether shows remarkable conformational adaptation corresponding to various natur...detailed

Degradation of TRIETHYLENE GLYCOL DIMETHYL ETHER (cas 112-49-2) by ozonation combined with UV irradiation or hydrogen peroxide addition08/22/2019

Ozonation of pure aqueous solutions of the polar aliphatic refractory triethylene glycol dimethyl ether (TEGDME) which is a typical representative of organic solutes of oil reclaiming wastewaters does not lead to effective mineralization unless high ozone doses are applied. Small doses of UV irr...detailed

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Continuous process for the preparation of alkylene glycol diethers

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