Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 90℃; for 9h; | 32% |
With sodium |
Conditions | Yield |
---|---|
at 210℃; under 36775.4 Torr; |
oxirane
ethylene glycol
A
Tetraethylene glycol
B
diethylene glycol
C
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
Conditions | Yield |
---|---|
at 130 - 210℃; unter Druck, 1 Mol Aethylenoxyd; |
oxirane
diethylene glycol
A
Tetraethylene glycol
B
Pentaethylene glycol
C
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
Conditions | Yield |
---|---|
unter Druck; |
Conditions | Yield |
---|---|
With acetic acid Verseifung das entstehenden Diacetat des Tetraaethylenglykols mit Baryt; |
Conditions | Yield |
---|---|
at 115 - 120℃; |
ethylene glycol
ethylene dibromide
A
Tetraethylene glycol
B
Pentaethylene glycol
C
diethylene glycol
D
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
Conditions | Yield |
---|---|
at 115 - 120℃; Produkt5: Hexaaethylenglykol; |
sodium 2-hydroxyethoxide
3-oxa-1,5-dichloropentane
Tetraethylene glycol
Conditions | Yield |
---|---|
at 65℃; |
Conditions | Yield |
---|---|
With water; hydrogenchloride In 1,4-dioxane Rate constant; Equilibrium constant; Ambient temperature; effect of alkali and alkaline earth metal chlorides and concentrations of HCl; |
2,2-diphenyl-1,3,6,9,12-pentaoxacyclotetradecane
Tetraethylene glycol
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 30℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), var. temp.; |
ethylene glycol
1,2-bis(2-chloroethoxy)ethane
A
Tetraethylene glycol
B
Pentaethylene glycol
Conditions | Yield |
---|---|
With potassium hydroxide at 140℃; for 120h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
In acetonitrile at 25℃; Rate constant; Equilibrium constant; different concentrations; |
iodine
diethylene glycol
A
Tetraethylene glycol
B
Pentaethylene glycol
C
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
Conditions | Yield |
---|---|
at 190℃; |
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With sulfuric acid at 90℃; |
Conditions | Yield |
---|---|
With iodine at 190℃; |
pentaethylene glycol
A
formic acid
B
Tetraethylene glycol
C
Pentaethylene glycol
D
ethylene glycol
E
acetic acid
F
diethylene glycol
G
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
Conditions | Yield |
---|---|
With titanium(IV) oxide In water for 24h; Concentration; UV-irradiation; |
Tetraethylene glycol
p-toluenesulfonyl chloride
tetraethylene glycol di(p-toluenesulfonate)
Conditions | Yield |
---|---|
With potassium hydroxide In dichloromethane at 0℃; for 3h; | 100% |
With potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 3h; | 100% |
With potassium hydroxide In dichloromethane at 0℃; for 3h; | 100% |
Tetraethylene glycol
p-toluenesulfonyl chloride
p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
Stage #1: Tetraethylene glycol With sodium hydroxide In tetrahydrofuran at 0℃; for 0.25h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 0℃; for 4h; | 100% |
Tetraethylene glycol
trityl chloride
1,1,1-triphenyl-2,5,8,11-tetraoxatridecan-13-ol
Conditions | Yield |
---|---|
With pyridine at 45℃; | 100% |
With pyridine at 45℃; for 16h; Etherification; | 99% |
With pyridine at 50℃; for 1h; | 89% |
Tetraethylene glycol
isonicotinoyl chloride hydrochloride
4-pyridinecarboxylic acid tetraethylene glycol diester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 4h; Condensation; Heating; | 100% |
Tetraethylene glycol
1-(bromomethyl)-4-(dodecyloxy)benzene
13-[4-(dodecyloxy)phenyl]-3,6,9,12-tetraoxatridecan-1-ol
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 4h; Heating; | 100% |
Tetraethylene glycol
(+)-(S)-6-Fluoro-3-methyl-4-(3-methyl-2-butenyl)-9-nitro-2,3,4,5-tetrahydro-1H-<1,4>benzodiazepine
(+)-(S)-6-(tetraethylene glycol)-3-methyl-4-(3-methyl-2-butenyl)-9-nitro-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine
Conditions | Yield |
---|---|
With potassium carbonate at 80℃; for 7h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With hydrogenchloride at 55℃; for 20h; pH=3; Inert atmosphere; | 100% |
Tetraethylene glycol
2-(2-methacryloyloxyethyloxy)ethyl isocyanate
Conditions | Yield |
---|---|
With dibutyltin dilaurate; 4-methoxy-phenol In diethyl ether at 40℃; for 12h; Flow reactor; | 99.7% |
With dibutyltin dilaurate; 4-methoxy-phenol In tetrahydrofuran at 75℃; for 5h; |
Tetraethylene glycol
2-Isocyanatoethyl methacrylate
Conditions | Yield |
---|---|
With dibutyltin dilaurate; 4-methoxy-phenol In diethyl ether at 40℃; for 12h; Solvent; Flow reactor; | 99.5% |
With dibutyltin dilaurate; 4-methoxy-phenol In tetrahydrofuran at 75℃; for 5h; |
Tetraethylene glycol
methanesulfonyl chloride
((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) dimethanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 10.75h; | 99% |
With triethylamine In dichloromethane at 20℃; for 24h; | 98% |
With triethylamine In dichloromethane at -5 - 20℃; | 98% |
Tetraethylene glycol
acrylonitrile
4,7,10,13,16-pentaoxanonadecane-1,14-dinitrile
Conditions | Yield |
---|---|
With potassium hydroxide for 1.5h; Michael addition; Cooling with ice; | 99% |
With potassium hydroxide In tetrahydrofuran at 20℃; for 1.5h; Michael Addition; | 99% |
Tetraethylene glycol
cis-1,2,3,6-tetrahydrophthalic anhydride
C24H34O11
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 9h; | 99% |
With base at 0 - 20℃; for 9h; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Dean-Stark; Large scale; | 99% |
Conditions | Yield |
---|---|
With proton-exchanged montmorillonite In neat (no solvent) at 100℃; for 5h; Reagent/catalyst; Time; | 99% |
Tetraethylene glycol
4-(bromomethyl)benzophenone
(4-(13-hydroxy-2,5,8,11-tetraoxatridecyl)phenyl)(phenyl)methanone
Conditions | Yield |
---|---|
Stage #1: Tetraethylene glycol With sodium hydride In tetrahydrofuran at 4 - 20℃; for 1h; Stage #2: 4-(bromomethyl)benzophenone In tetrahydrofuran at 20℃; for 16h; | 98.8% |
Stage #1: Tetraethylene glycol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-(bromomethyl)benzophenone In tetrahydrofuran at 0 - 20℃; | 65% |
1,4-bis(bromomethyl)benzene
Tetraethylene glycol
1,4-bis(13-hydroxy-2,5,8,11-tetraoxatridecyl)benzene
Conditions | Yield |
---|---|
With sodium Williamson etherification; | 98% |
With sodium hydride at 40℃; for 48h; | 71% |
With potassium carbonate In acetone for 15h; Heating; | 53% |
With sodium 1.) 50 deg C; 2.) 60 deg C, 18 h; Yield given. Multistep reaction; |
Tetraethylene glycol
propargyl bromide
1,11-bis(2-propyn-1-oxy)-3,6,9-trioxaundecane
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; water; sodium hydroxide In toluene at 45 - 60℃; for 7h; Inert atmosphere; | 98% |
Stage #1: Tetraethylene glycol With sodium hydride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 23℃; for 48h; Inert atmosphere; | 94% |
Stage #1: Tetraethylene glycol With sodium hydride In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; hexane at -78 - 20℃; for 6h; | 79% |
Tetraethylene glycol
1,11-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3,6,9-trioxaundecane-1,11-dione
Conditions | Yield |
---|---|
In chlorobenzene Heating; | 98% |
Conditions | Yield |
---|---|
With triethylamine at 180℃; for 23h; | 98% |
With triethylamine | 93% |
With triethylamine In dichloromethane at 180℃; | 91% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 9h; | 98% |
Conditions | Yield |
---|---|
With potassium hydroxide In dichloromethane at 0 - 20℃; for 3h; | 98% |
Tetraethylene glycol
Conditions | Yield |
---|---|
at 20℃; for 0.5h; | 97% |
Conditions | Yield |
---|---|
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; for 20h; Inert atmosphere; Cooling; | 97% |
Multi-step reaction with 3 steps 1: 44 percent / PBr3, pyridine 2: 66 percent / dimethylformamide 3: 48 percent / 1) hydrazine hydrate, 2) 6N aq. HCl / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 85 percent / Ph3P, CBr4 / acetonitrile / 18 h / 40 °C 2: 93 percent / NaN3 / dimethylformamide / 100 h / 100 °C 3: 93 percent / H2 / Pd/BaSO4 / ethanol; H2O / 30 h / 760 Torr View Scheme |
Tetraethylene glycol
toluene-4-sulfonic acid
p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 4h; | 97% |
With pyridine In dichloromethane at 25℃; for 20h; | 81% |
With pyridine at 20℃; for 6h; | 30% |
Conditions | Yield |
---|---|
With triethylamine at 180℃; for 18h; | 97% |
Tetraethylene glycol
ethyl acetate
bis-[2-(2-acetoxy-ethoxy)-ethyl]-ether
Conditions | Yield |
---|---|
With C16H25N3O2S for 36h; Molecular sieve; Reflux; | 97% |
With C16H25N3O2S for 36h; Reflux; Molecular sieve; | 97% |
3-Bromomethylthiophene
Tetraethylene glycol
Conditions | Yield |
---|---|
With sodium hydride; potassium iodide In tetrahydrofuran at 50℃; for 11h; Williamson Ether Synthesis; Cooling with ice; Inert atmosphere; | 96% |
With sodium hydride In tetrahydrofuran Heating; | 57% |
With sodium hydride; potassium iodide In tetrahydrofuran Reflux; |
Tetraethylene glycol
7-chloromethylhinokitiol
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane Ambient temperature; | 96% |
Tetraethylene glycol
(E)-3-hexene-1,6-dioic acid
poly(tetraethylene glycol hydromuconoate), polycondensation, Mn = 5600 g/mol (GPC), PDI = 1.8 (GPC); monomer(s): trans-β-hydromuconic acid; tetraethylene glycol
Conditions | Yield |
---|---|
stannous octoate under 20 Torr; for 24h; | 96% |
Tetraethylene glycol
methanesulfonyl chloride
1-phenyl-2,5,8,11-tetraoxatridecan-13-yl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -30 - 0℃; for 3h; | 96% |
Reported in EPA TSCA Inventory.
The Tetraethylene glycol, with the CAS registry number 112-60-7, is also known as Bis[2-(2-hydroxyethoxy)ethyl] ether. It belongs to the product categories of Ethylene Glycols; Ethylene Glycols & Monofunctional Ethylene Glycols. Its EINECS registry number is 203-989-9. This chemical's molecular formula is C8H18O5 and molecular weight is 194.23. Its IUPAC name is called 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethanol. This chemical's classification codes are Mutation data; Skin / Eye Irritant. It is colorless to straw-colored liquid. In addition, it should be stored in a cool, ventilated warehouse and kept away from fire and heat.
Physical properties of Tetraethylene glycol: (1)ACD/LogP: -2.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.23; (4)ACD/LogD (pH 7.4): -2.23; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.46; (8)ACD/KOC (pH 7.4): 1.46; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 12; (12)Index of Refraction: 1.455; (13)Molar Refractivity: 47.41 cm3; (14)Molar Volume: 174.6 cm3; (15)Surface Tension: 41.3 dyne/cm; (16)Density: 1.111 g/cm3; (17)Flash Point: 176.7 °C; (18)Enthalpy of Vaporization: 66.1 kJ/mol; (19)Boiling Point: 328 °C at 760 mmHg; (20)Vapour Pressure: 1.47E-05 mmHg at 25°C.
Uses of Tetraethylene glycol: it can be used in organic synthesis as a solvent, hot carrier and gas chromatography stationary phase. Besides, it can be used with drying solvents, moisturizing agents, softening agents, nitro spray, etc.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. You should avoid contacting it with skin and eyes.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C(COCCOCCOCCO)O
(2)InChI: InChI=1S/C8H18O5/c9-1-3-11-5-7-13-8-6-12-4-2-10/h9-10H,1-8H2
(3)InChIKey: UWHCKJMYHZGTIT-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 20gm/kg (20000mg/kg) | Union Carbide Data Sheet. Vol. 3, Pg. 3, 1969. | |
rat | LD50 | oral | 28900uL/kg (28.9mL/kg) | Union Carbide Data Sheet. Vol. 3/3/1969, |
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