143-24-8

Basic information

• Product Name: Tetraethylene glycol dimethyl ether
• Synonyms: 1-(2-methoxyethoxy)-2-[2-(2-methoxyethoxy)-ethoxy]-ethane;1,11-dimethoxy-3,6,9-trioxa-undecane;Ansol E-181;Ansul Ether 181AT;ansulether181at;e181(ether);Ether, bis[2-(2-methoxyethoxy)ethyl];ether,bis(2-(2-methoxyethoxy)ethyl)
• CAS NO: 143-24-8
• Molecular Formula: C₁₀H₂₂O₅
• Molecular Weight: 222.28
• EINECS: 205-594-7
• Product Categories: Aliphatics;Alkyl;Biomaterials;Crosslinking Agents;Homobifunctional PEGs;Materials Science;Poly(ethylene glycol) and Poly(ethylene oxide);Polymer Science;Polymers;Building Blocks;C10;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 143-24-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: −30 °C(lit.)
• Boiling Point: 275-276 °C(lit.)
• Flash Point: 285 °F
• Appearance: Clear/Liquid
• Density: 1.009 g/mL at 25 °C(lit.)
• Vapor Density: 7.7 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Explosive Limit: 0.8%(V)
• Water Solubility: Soluble
• Merck: 14,9208
• BRN: 1760005
• CAS DataBase Reference: Tetraethylene glycol dimethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraethylene glycol dimethyl ether(143-24-8)
• EPA Substance Registry System: Tetraethylene glycol dimethyl ether(143-24-8)

Safety Data

• Hazard Codes: Xi
• Statements: 19-43-62-61
• Safety Statements: 36-24-45-36/37-53-26
• WGK Germany: 1
• RTECS: SB0400000
• TSCA: Yes
• Hazardous Substances Data: 143-24-8(Hazardous Substances Data)

Usage

Chemical Properties

clear liquid

Uses

Different sources of media describe the Uses of 143-24-8 differently. You can refer to the following data:
1. Tetraethylene glycol dimethyl ether is used as a solvent.
2. Solvent.
3. Tetraethylene glycol dimethyl ether is used in lithium-ion battery technology. It is associated with trifluoroethanol and used as a working pair for organic absorption heat pumps. It acts as a solvent for cleaning and degreasing due to its chemical and thermal stability. Moreover, it is suitable solvent for high temperature reactions due its high boiling point. Further, it is used in the selective adsorption of proteins during the promotion of cell adhesion.

General Description

Tetraethylene glycol dimethyl ether or tetraglyme is an organic aprotic colourless solvent with film forming ability.

Flammability and Explosibility

Nonflammable

Safety Profile

Mildly toxic by ingestion. Experimental reproductive effects. An eye irritant. Many glycol ethers are suspected of having dangerous human reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS

Purification Methods

Stand the ether over CaH2, LiAlH4 or sodium, and distil it when required. [Beilstein 1 IV 2404.]

InChI:InChI=1/C8H18O5.C2H6O/c9-1-3-11-5-7-13-8-6-12-4-2-10;1-3-2/h9-10H,1-8H2;1-2H3

Synthetic route

cyclohexano-15-crown-5 ether (17454-48-7, 62623-99-8) + methyl iodide (74-88-4) → Tetraethylene glycol dimethyl ether (143-24-8) + 2-(9-methoxy-1,4,7-trioxanonyl)cyclohexyl methyl ether + 2-[[2-(methoxy)ethoxy]ethoxy]-1-[(2-methoxy)ethoxy]cyclohexane

Conditions	Yield
Stage #1: cyclohexano-15-crown-5 ether With potassium mirror In tetrahydrofuran at 20℃; for 0.416667h; Stage #2: methyl iodide In tetrahydrofuran Further stages.;	A 15% B 38% C 29%

1,11-dichloro-3,6,9-trioxaundecane (638-56-2) + sodium methylate (124-41-4) → Tetraethylene glycol dimethyl ether (143-24-8)

Conditions	Yield
With methanol

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → Tetraethylene glycol dimethyl ether (143-24-8)

Conditions	Yield
With sodium hydroxide; sulfuryl dichloride a) 10 deg C, 1 h, b) 100 deg C, 1 h;	0.70 mol

1-(2-Methoxy-ethoxy)-2-[2-(2-methoxy-ethoxy)-ethoxy]-ethane; compound with GENERIC INORGANIC NEUTRAL COMPONENT → Tetraethylene glycol dimethyl ether (143-24-8)

Conditions	Yield
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant;

3-oxa-1,5-dichloropentane (111-44-4) + sodium salts of ethylene glycol-monomethyl ether → Tetraethylene glycol dimethyl ether (143-24-8)

Conditions	Yield
zuletzt bei 110-115grad;

tetraethylene glycol dimethyl ether and lithium picrate complex → Tetraethylene glycol dimethyl ether (143-24-8) + lithium picrate-RG7

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

tetraethylene glycol dimethyl ether and sodium picrate complex → Tetraethylene glycol dimethyl ether (143-24-8) + sodium picrate-RG7

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

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;

Allyl glycidyl ether (106-92-3) + 15-crown-5 (33100-27-5) + methyl iodide (74-88-4) → glycidyl methyl ether (930-37-0) + Tetraethylene glycol dimethyl ether (143-24-8) + tetraethylene glycol methyl vinyl ether + 6-allyloxy-5-methoxy-hex-1-ene

Conditions	Yield
Stage #1: 15-crown-5 With potassium In tetrahydrofuran at 25℃; for 0.416667h; Stage #2: Allyl glycidyl ether In tetrahydrofuran Stage #3: methyl iodide In tetrahydrofuran Further byproducts given. 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;

Tetraethylene glycol dimethyl ether (143-24-8) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → C2F6NO4S2(1-)*Li(1+)*C10H22LiO5(1+)

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

Tetraethylene glycol dimethyl ether (143-24-8) + lithium perchlorate → Li(1+)*C10H22LiO5(1+)*ClO4(1-)

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

Tetraethylene glycol dimethyl ether (143-24-8) + lithium trifluoromethanesulfonate (33454-82-9) → Li(1+)*C10H22LiO5(1+)*CF3O3S(1-)

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

lithium tetrafluoroborate + Tetraethylene glycol dimethyl ether (143-24-8) → Li(1+)*C10H22LiO5(1+)*BF4(1-)

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

ammonium iodide + copper(l) iodide (7681-65-4) + barium iodide dihydrate + Tetraethylene glycol dimethyl ether (143-24-8) → [Ba(tetraglyme)2][Cu2I4]

Conditions	Yield
In acetone for 4h; Schlenk technique; Inert atmosphere;	99%

Tetraethylene glycol dimethyl ether (143-24-8) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → lithium tetraethylene glycol dimethyl ether bis(trifluoromethanesulfonyl)imide

Conditions	Yield
In dichloromethane for 48h; Inert atmosphere;	99%
In diethyl ether at 60℃; Inert atmosphere;
at 60℃; for 3h;

Tetraethylene glycol dimethyl ether (143-24-8) + Er(3+)*3C4H9COCHCOC4H9(1-)*H2O=[Er(C4H9COCHCOC4H9)3(H2O)] → [(Er(C4H9COCHCOC4H9)3)2(CH3O(CH2CH2O)4CH3)]

Conditions	Yield
In hexane stirring (10 min); crystn. (room temp.); elem. anal.;	97%

Tetraethylene glycol dimethyl ether (143-24-8) + manganese(II) bistriflimide hexahydrate → [manganese(II)(tetraglyme)] bistriflimide

Conditions	Yield
In acetonitrile at 20℃; for 1h;	97%

diethyl ether (60-29-7) + Tetraethylene glycol dimethyl ether (143-24-8) + yttrium(III) trifluoroacetate trihydrate + sodium hydride (7646-69-7) + trifluoroacetic acid (76-05-1) → [YNa2(trifluoroacetate)5(tetraglyme)]*0.5(diethyl ether)

Conditions	Yield
In tetrahydrofuran under Ar; soln. of NaH (3.91 mmol) and CF3COOH (1.66 mmol) in THF added dropwise to soln. of Y compd. (1.66 mmol) in THF, tetraglyme (1.72 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.;	96%
In tetrahydrofuran under Ar; soln. of NaH (1.64 mmol) and CF3COOH (1.65 mmol) in THF added dropwise to soln. of Y compd. (1.63 mmol) in THF, tetraglyme (3.26 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.;	94%

{La((CH3)3CCOCHCOC(CH3)3)3(H2O)} + Tetraethylene glycol dimethyl ether (143-24-8) → {La((CH3)3CCOCHCOC(CH3)3)3C10H22O5}

Conditions	Yield
In hexane under N2: dissolving of 0.74 mmol (La(C(CH3)3COCHCOC(CH3)3)3(H2O)) in hexane; addn. of 0.74 mmol tetraglyme; stirring for 1 h;; removing of solvent in vac.; storing under vac. at 65°C for 1 h; cooling to room temperature; crystallization within 2 d; elem. anal.;;	95%

diethyl ether (60-29-7) + ytterbium(III) trifluoroacetate trihydrate + Tetraethylene glycol dimethyl ether (143-24-8) + sodium hydride (7646-69-7) + trifluoroacetic acid (76-05-1) → [Na2Yb(trifluoroacetate)5(tetraglyme)]*0.5(diethyl ether)

Conditions	Yield
In tetrahydrofuran under Ar; soln. of NaH (0.82 mmol) and CF3COOH (0.82 mmol) in THF added dropwise to soln. of Yb compd. (0.40 mmol) in THF, tetraglyme (0.45 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.;	95%

ammonium iodide + barium iodide dihydrate + Tetraethylene glycol dimethyl ether (143-24-8) + silver(I) iodide → [Ba(tetraglyme)2]2[Ag4I8]

Conditions	Yield
In acetone for 4h; Schlenk technique; Inert atmosphere;	93%

Tetraethylene glycol dimethyl ether (143-24-8) + tin(II) bromide → C10H22O5*2Sn(2+)*4Br(1-)

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	92%

Tetraethylene glycol dimethyl ether (143-24-8) + 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3,3-dimethylbutan-1-one → 2C16H19N2O2(1-)*C10H22O5*Sr(2+)

Conditions	Yield
With strontium In ethanol for 1h;	91%

diethyl ether (60-29-7) + erbium(III) trifluoroacetate trihydrate + Tetraethylene glycol dimethyl ether (143-24-8) + sodium hydride (7646-69-7) + trifluoroacetic acid (76-05-1) → [Na2Er(trifluoroacetate)5(tetraglyme)]*0.5(diethyl ether)

Conditions	Yield
In tetrahydrofuran under Ar; soln. of NaH (1.62 mmol) and CF3COOH (1.68 mmol) in THF added dropwise to soln. of Er compd. (0.80 mmol) in THF, tetraglyme (0.82 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.;	91%

sodium molybdate dihydrate (7631-95-0) + Tetraethylene glycol dimethyl ether (143-24-8) + hydrogen bromide (10035-10-6, 12258-64-9) → MoO2Br2(H2O)2*(C10H22O5)

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.;	90%

tin(II) trifluoromethanesulfonate + Tetraethylene glycol dimethyl ether (143-24-8) → Sn(OTf)2*tetraglyme (1361343-34-1)

Conditions	Yield
In acetonitrile (inert atmosphere); a soln. of ligand added dropwise to a soln. of Sn salt, stirred overnight; concd. (vac.), rinsed and sonicated with ether/pentane; elem. anal.;	90%

ammonia borane complex (10043-11-5) + Tetraethylene glycol dimethyl ether (143-24-8) → C10H22O5*2BH6N

Conditions	Yield
at 20 - 45℃; Schlenk technique;	89%

lanthanum(III) oxide + Tetraethylene glycol dimethyl ether (143-24-8) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) → [La(CF3COCHCOCF3)3(C10H22O5)] (207130-26-5)

Conditions	Yield
In hexane addn. of tetraglyme to La2O3 in hexane, addn. of CF3COCH2COCF3; filtration, slight redn. of volume, , filtration, drying (vac.), recrystn. (hexane); elem. anal.;	88%

thallium(I) carbonate + Tetraethylene glycol dimethyl ether (143-24-8) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) → [Tl(1,1,1,5,5,5-hexafluoro-2,4-pentanedionate)(tetraglyme)]

Conditions	Yield
In dichloromethane glyme was added to suspn. of Tl2CO3 in CH2Cl2; hexafluoroacetylacetone was added; filtered; evapd.; septd.; hexane added; filtered; dried (vac.); elem. anal.;	88%

Tetraethylene glycol dimethyl ether (143-24-8) + acetic anhydride (108-24-7) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With zinc(II) triflate at 130℃; for 24h; Reagent/catalyst;	88%

Tetraethylene glycol dimethyl ether (143-24-8) + ({Sr[O(SiPh2O)2](H2O)(NH3)}n) → {Sr3[O(SiPh2O)2]3(tetraglyme)2}

Conditions	Yield
In toluene at 110℃; for 3h;	87%

Tetraethylene glycol dimethyl ether (143-24-8) + 4-benzoyl-3-methyl-1-phenylpyrazol-5-one (33064-14-1) → 2C17H13N2O2(1-)*C10H22O5*Sr(2+)

Conditions	Yield
With strontium In ethanol	87%

oxirane (75-21-8) + methanol (67-56-1) + Tetraethylene glycol dimethyl ether (143-24-8) + carbon monoxide (201230-82-2) → methyl ester (3-hydroxy) propionic acid (6149-41-3)

Conditions	Yield
1H-imidazole; dicobalt octacarbonyl at 80℃; under 60006 Torr; for 2h; Heating / reflux;	82.44%

Tetraethylene glycol dimethyl ether (143-24-8) + bis(diphenylthiophosphinoyl)amine (6588-07-4) → C24H20NP2S2(1-)*C10H22O5*Na(1+)

Conditions	Yield
With sodium hydroxide In methanol; water for 0.5h; Addition;	82%

sodium metavanadate + Tetraethylene glycol dimethyl ether (143-24-8) → {V(tetraethylene glycol)(Br)2}Br (123027-46-3)

Conditions	Yield
With hydrogen bromide In 1,2-dichloro-ethane gaseous HBr bubbled through the soln. for 15 min, stored in a sealed vial at room temp. for 2-5 days (exclusion of air); elem. anal.;	82%

cerium(III) chloride heptahydrate + Tetraethylene glycol dimethyl ether (143-24-8) + 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5,octanedione (17587-22-3) → 2Ce(3+)*6CF3CF2CF2C(O)CHC(O)C(CH3)3(1-)*CH3O(CH2CH2O)4CH3=Ce2(C3F7C(O)CHC(O)C(CH3)3)6(CH3O(CH2CH2O)4CH3)

Conditions	Yield
With NaOH In ethanol; water filtering, concg., CH2Cl2 addn., decanting, pptn. on concg., filtering, evapn.; elem. anal.;	82%

oxirane (75-21-8) + Tetraethylene glycol dimethyl ether (143-24-8) + carbon monoxide (201230-82-2) → 2-methoxy-ethanol (109-86-4) + methyl ester (3-hydroxy) propionic acid (6149-41-3) + methyl β-(β-hydroxypropionyloxy)propionate (27313-49-1) + acetaldehyde (75-07-0)

Conditions	Yield
3-HYDROXYPYRIDINE; dicobalt octacarbonyl at 75℃; under 45004.5 Torr; for 4h; Heating / reflux;	A n/a B 81.08% C n/a D n/a

cerium(III) chloride heptahydrate + Tetraethylene glycol dimethyl ether (143-24-8) + ethyl 4,4,4-trifluoroacetoacetate (372-31-6) → Ce2(CF3C(O)CHC(O)OC2H5)6(CH3O(CH2CH2O)4CH3)

Conditions	Yield
With NaOH In ethanol; water filtering, concg., CH2Cl2 addn., decanting, pptn. on concg., filtering, evapn.; elem. anal.;	81%

Tetraethylene glycol dimethyl ether (143-24-8) + benzoyl chloride (98-88-4) → 2-chloroethyl benzoate (939-55-9)

Conditions	Yield
With zinc(II) chloride at 130℃; for 24h; Neat (no solvent);	81%

Upstream product

• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 17454-48-7 cyclohexano-15-crown-5 ether 
• 74-88-4 methyl iodide 
• 2426-08-6 glycidyl n-butyl ether 
• 33100-27-5 15-crown-5 
• 106-92-3 Allyl glycidyl ether 
• 115-10-6 Dimethyl ether 
• 75-21-8 oxirane 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 638-56-2 1,11-dichloro-3,6,9-trioxaundecane 
• 124-41-4 sodium methylate 

Downstream Products

• 64028-06-4 F-tetraethylene glycol dimethyl ether 
• 67-56-1 methanol 
• 107-25-5 methoxyethene 
• 1663-35-0 2-methoxyethyl vinyl ether 
• 4413-28-9 vinyl methyl ether of diethylene glycol 
• 109-86-4 2-methoxy-ethanol 
• 6149-41-3 methyl ester (3-hydroxy) propionic acid 
• 27313-49-1 methyl β-(β-hydroxypropionyloxy)propionate 
• 75-07-0 acetaldehyde 
• 123-91-1 1,4-dioxane 
• 110-71-4 1,2-dimethoxyethane 

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Effect of Tetraethylene glycol dimethyl ether (cas 143-24-8) on Electrical, Structural and Thermal Properties of PVA-Based Polymer Electrolyte for Magnesium Battery09/30/2019

The aim of the contribution is to introduce a high performance magnesium conducting polymer electrolytes (PEs) comprising hybrid of poly(vinyl alcohol) (PVA), magnesium bromide (MgBr_2) and tetraethylene glycol dimethyl ether (TEGDME) as plasticizer are prepared at various compositions by soluti...detailed

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To realize a high-performance room temperature Na/S battery with an elemental sulfur cathode, it is important that sodium polysulfides stay within the cathode and that they have room enough to react freely. In this work, sodium polysulfides are confined to the cathode using a β″ alumina solid ...detailed

Relevant articles and documents

METHOD FOR THE PRODUCTION OF POLYOXYMETHYLENE DIALKYL ETHERS FROM TRIOXAN AND DIALKYLETHERS

The invention relates to a method for production of polyoxymethylene dialkyl ethers of formula H2m+1CmO(CH2O)nCmH2m+1, where n = 2 - 10, m independently = 1 or 2, in which a dialkyl ether selected from dimethyl ether, methyl ethyl ether or diethyl ether and trioxan are fed into a reactor and reacted in the presence of an acid catalyst, whereby the amount of water introduced into the reaction mixture with the dialkyl ether, trioxan and/or the catalyst is 1 wt. %, with relation to the reaction mixture.

Cleavage of different ether bonds in butyl glycidyl ether and allyl glycidyl ether by K-, K+ (15-crown-5)2

The kind of substituent in alkyl glycidyl ethers affects the course of their reaction with K1, K+ (15-crown-5)2. The cyclic oxirane ring is exclusively cleaved in the case of butyl glycidyl ether whereas the presence of the unsaturated allyl group in the glycidyl ether molecule unexpectedly prefers the scission of the linear ether bond. In both the systems organometallic intermediates are formed. They react with crown ether causing its ring opening. Allylpotassium formed from allyl glycidyl ether reacts also with another glycidyl ether molecule; the oxirane ring is opened in this case.

SYNTHESIS OF DIALKYL ETHERS OF POLYETHYLENE GLYCOLS

Methods were developed for synthesis of dimethyl and diethyl ethers of polyethylene glycols in one step (without isolation of intermediates) with the general formula R(OC2H4)mOR, where R=CH3, C2H5 and m=2-6 (degree of polyglycolicity).As starting materials monomethyl and monoethyl ethers of polyethylene glycols of the formula R(OC2H4)nOH were used, where n=1-3.As reagents toluenesulfonyl chloride and methanesulfonyl chloride were used.