Conditions | Yield |
---|---|
With sodium In diethyl ether for 6h; Heating; | 70% |
ethylene glycol
acetylene
A
ethylene glycol divinyl ether
B
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With sodium hydroxide; cesium fluoride In dimethyl sulfoxide at 100℃; for 6h; | A 37% B 12% |
With potassium hydroxide; nitrogen at 120℃; under 11032.6 - 22065.2 Torr; | |
With potassium hydroxide; nitrogen at 120℃; under 11032.6 - 22065.2 Torr; |
ethylene glycol
acetylene
A
2-methyl-1,3-dioxolane
B
ethylene glycol divinyl ether
C
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With sodium hydroxide; cesium fluoride at 138 - 142℃; under 10297.1 Torr; for 3.5h; | A 4% B 11% C 26% |
2-(2-vinyloxy-ethoxy)-[1,3,2]dioxaphospholane
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With potassium hydroxide |
2-[2-(ethenyloxy)ethoxy]ethan-1-ol
A
2-methyl-1,3-dioxolane
B
ethanol
C
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With potassium hydroxide at 170 - 250℃; Product distribution; |
diethylene glycol
A
formaldehyd
B
ethanol
C
ethene
D
2-hydroxyethyl vinyl ether
E
acetaldehyde
Conditions | Yield |
---|---|
With oxygen at 400℃; for 0.333333h; Product distribution; |
1,4-dioxane
A
trimethylene oxide
B
formaldehyd
C
ethene
D
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
Mechanism; Product distribution; Quantum yield; Irradiation; 185 nm vacuum-ultraviolet photolysis; |
ethylene glycol
acetylene
A
ethylene glycol divinyl ether
B
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
at 180℃; unter Druck; | |
at 120℃; unter Druck; | |
at 120℃; unter Druck; | |
at 180℃; unter Druck; |
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With diethyl ether; sodium |
Vinyl bromide
ethylene glycol
A
ethylene glycol divinyl ether
B
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
at 120℃; unter Druck; |
ethylene glycol
A
ethylene glycol divinyl ether
B
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
at 120℃; unter Druck; |
Conditions | Yield |
---|---|
With potassium hydroxide at 150℃; for 4h; Autoclave; |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at -20 - 20℃; for 2h; | 100% |
With triethylamine In dichloromethane at 4℃; for 12h; | 76% |
2-hydroxyethyl vinyl ether
bis(1,3-dioxolan-2-ylmethyl)selenide
Conditions | Yield |
---|---|
Stage #1: ethyleneglycol vinyl ether In chloroform at -20 - 20℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In chloroform at 20℃; for 6h; Reagent/catalyst; | 100% |
2-hydroxyethyl vinyl ether
2-propanesulfonyl chloride
1-vinyloxethyl propane 2-sulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 97.7% |
Conditions | Yield |
---|---|
With 1,3-bis-(diphenylphosphino)propane; triethylammonium tetrafluoroborate; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate; diisopropylamine at 115℃; for 2h; Heck arylation; | 97% |
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In ethylene glycol at 145℃; for 2h; Heck reaction; Inert atmosphere; regioselective reaction; | 88% |
With 1,3-bis-(diphenylphosphino)propane; triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate at 115℃; for 18h; Heck reaction; | 83% |
With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; thallium(I) acetate; triethylamine In N,N-dimethyl-formamide at 80℃; for 144h; | 81% |
Conditions | Yield |
---|---|
Stage #1: ethyleneglycol vinyl ether; para-bromoacetophenone With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In isopropyl alcohol at 115℃; Heck reaction; Inert atmosphere; Stage #2: With hydrogenchloride; water In isopropyl alcohol for 0.5h; | 97% |
2-hydroxyethyl vinyl ether
bromostyrene
(E)-2-methyl-2-styryl-1,3-dioxolane
Conditions | Yield |
---|---|
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In dimethyl sulfoxide at 115℃; for 4h; Heck vinylation; Inert atmosphere; regioselective reaction; | 97% |
5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); N-Methyldicyclohexylamine In 1,4-dioxane at 25℃; for 16h; | 97% |
2-hydroxyethyl vinyl ether
2-propynyl chloride
ethylene glycol vinyl propargyl diether
Conditions | Yield |
---|---|
With sodium hydroxide; tributyl-amine In water at 50 - 60℃; for 3h; Product distribution; other catalyst; | 96.8% |
With sodium hydroxide; tributyl-amine In water at 50 - 60℃; for 3h; | 96.8% |
o-fluorobromobenzene
2-hydroxyethyl vinyl ether
2-(2-fluorophenyl)-2-methyl-1,3-dioxolane
Conditions | Yield |
---|---|
With 1,3-bis-(diphenylphosphino)propane; triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate at 115℃; for 24h; Heck reaction; | 96% |
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In ethylene glycol at 145℃; Heck reaction; Inert atmosphere; regioselective reaction; | 77% |
2-hydroxyethyl vinyl ether
1-Bromo-4-fluorobenzene
2-(4-fluorophenyl)-2-methyl-1,3-dioxolane
Conditions | Yield |
---|---|
With 1,3-bis-(diphenylphosphino)propane; triethylammonium tetrafluoroborate; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate; diisopropylamine at 115℃; for 2h; Heck arylation; | 96% |
With 1,3-bis-(diphenylphosphino)propane; triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate at 115℃; for 24h; Heck reaction; | 86% |
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In ethylene glycol at 145℃; Heck reaction; Inert atmosphere; regioselective reaction; | 85% |
2-hydroxyethyl vinyl ether
4-Ethynyl-benzoic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 18h; Inert atmosphere; | 96% |
2-hydroxyethyl vinyl ether
4-fluorobenzalaniline
Conditions | Yield |
---|---|
Stage #1: 4-fluorobenzalaniline With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; magnesium sulfate In toluene at -10℃; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: ethyleneglycol vinyl ether In toluene at -10℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry; enantioselective reaction; | 96% |
2-hydroxyethyl vinyl ether
p-toluenesulfonyl chloride
toluene-4-sulfonic acid 2-vinyloxy-ethyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 4h; | 95.46% |
With dmap; triethylamine In dichloromethane | 94% |
With pyridine at 0℃; for 1h; | 90% |
With dmap; triethylamine In dichloromethane for 48h; | 65% |
With pyridine In acetone |
Conditions | Yield |
---|---|
With sodium hydroxide; PEG-1 In water at 20℃; for 6.5h; Product distribution; other time, other temperature, other ratio, without catalyst; | 95.3% |
With sodium hydroxide; PEG-1 In water at 20℃; for 6.5h; | 95.3% |
Conditions | Yield |
---|---|
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 95℃; for 4h; Inert atmosphere; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
With copper(l) iodide; sodium t-butanolate In N,N-dimethyl-formamide for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Heating; | 95% |
2-hydroxyethyl vinyl ether
4-bromobenzenecarbonitrile
4-(2-methyl-[1,3]dioxolan-2-yl)benzonitrile
Conditions | Yield |
---|---|
With 1,3-bis-(diphenylphosphino)propane; triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate at 115℃; for 24h; Heck reaction; | 94% |
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In ethylene glycol at 145℃; Heck reaction; Inert atmosphere; regioselective reaction; | 86% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); diphenyl diselenide In neat (no solvent) heating a mixt. of tin compd., alkene, Se compd. and AIBN at 80°Cfor 2.5 h with stirring; | 94% |
With 2,2'-azobis(isobutyronitrile) In neat (no solvent) heating a mixt. of tin compd., alkene and AIBN at 80°C for 2.5 h with stirring; | 77% |
5-bromo-3-pyridine carboxylic acid methyl ester
2-hydroxyethyl vinyl ether
C11H13NO4
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine at 140℃; for 2h; Heck reaction; | 94% |
2-hydroxyethyl vinyl ether
4-(1H-1,2,4-triazol-1-yl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: ethyleneglycol vinyl ether With isopropylmagnesium bromide In diethyl ether at 25℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: 4-(1H-1,2,4-triazol-1-yl)benzaldehyde With scandium tris(trifluoromethanesulfonate) at 40℃; for 20h; Schlenk technique; Inert atmosphere; | 94% |
2-hydroxyethyl vinyl ether
N-(2-bromobenzylidene)aniline
Conditions | Yield |
---|---|
Stage #1: N-(2-bromobenzylidene)aniline With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; magnesium sulfate In toluene at -10℃; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: ethyleneglycol vinyl ether In toluene at -10℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry; enantioselective reaction; | 94% |
4'-Bromopropiophenone
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With cis,cis,cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 130℃; for 20h; | A 93% B 5 % Spectr. |
Conditions | Yield |
---|---|
Stage #1: ethyleneglycol vinyl ether; 2-bromonaphthalene With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In isopropyl alcohol at 115℃; Heck reaction; Inert atmosphere; Stage #2: With hydrogenchloride; water In isopropyl alcohol for 0.5h; | 93% |
Conditions | Yield |
---|---|
Stage #1: ethyleneglycol vinyl ether With isopropylmagnesium bromide In diethyl ether at 25℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: 2-formylbenzo[b]furan With scandium tris(trifluoromethanesulfonate) at 40℃; for 12h; Schlenk technique; Inert atmosphere; | 93% |
2-hydroxyethyl vinyl ether
methyl 3-((phenylimino)methyl)benzoate
Conditions | Yield |
---|---|
Stage #1: methyl 3-((phenylimino)methyl)benzoate With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; magnesium sulfate In toluene at -10℃; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: ethyleneglycol vinyl ether In toluene at -10℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry; enantioselective reaction; | 93% |
1-bromo-butane
2-hydroxyethyl vinyl ether
ethylene glycol n-butyl vinyl diether
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water | 92.1% |
2-hydroxyethyl vinyl ether
4-bromobenzenecarbonitrile
A
4-(2-methyl-[1,3]dioxolan-2-yl)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 130℃; for 20h; Heck reaction; | A n/a B 92% |
With cis,cis,cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 130℃; for 20h; | A 2 % Spectr. B 92% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In ethylene glycol at 140℃; for 2h; Heck reaction; | 92% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine at 140℃; for 1h; Heck reaction; | 92% |
2-hydroxyethyl vinyl ether
(E)-4-(2-bromo-vinyl)-anisole
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; diphenylphosphino(diphenylphosphonyl)propane In dimethyl sulfoxide at 115℃; for 1h; Heck vinylation; Inert atmosphere; regioselective reaction; | 92% |
Glycol ether compounds are on the Community Right-To-Know List.
The CAS registry number of Ethylene glycol monovinyl ether is 764-48-7. The systematic name is 2-(ethenyloxy)ethanol. In addition, the molecular formula is C4H8O2 and the molecular weight is 88.11. It belongs to the classes of Ethylene Glycols Monofunctional Ethylene Glycols and Monofunctional Ethylene Glycols. What's more, it should be stored in a cool and dry place.
Physical properties about this chemical are: (1)ACD/LogP: -0.27; (2)ACD/LogD (pH 5.5): -0.27; (3)ACD/LogD (pH 7.4): -0.27; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 16.93; (7)ACD/KOC (pH 7.4): 16.93; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 18.46 Å2; (12)Index of Refraction: 1.418; (13)Molar Refractivity: 23.58 cm3; (14)Molar Volume: 93.5 cm3; (15)Polarizability: 9.35 ×10-24cm3; (16)Surface Tension: 28.8 dyne/cm; (17)Density: 0.942 g/cm3; (18)Flash Point: 50 °C; (19)Enthalpy of Vaporization: 43.25 kJ/mol; (20)Boiling Point: 133.7 °C at 760 mmHg; (21)Vapour Pressure: 3.64 mmHg at 25°C.
Preparation of Ethylene glycol monovinyl ether: it can be prepared by ethane-1,2-diol and ethyne. The other product is 1,2-bis-vinyloxy-ethane. This reaction will need reagents CsF and NaOH and solvent dimethylsulfoxide. The reaction time is 6 hours at reaction temperature of 100 °C. The yield is about 37%.
Uses of Ethylene glycol monovinyl ether: it can be used to get 2-methyl-[1,3]dioxolane. This reaction will need reagent KOH. And it needs cyclization and various alkalis. The yield is about 51% at reaction temperature of 120 °C.
When you are using this chemical, please be cautious about it as the following:
This chemical is flammable. During using it, wear suitable protective clothing. And you should keep away from sources of ignition.
You can still convert the following datas into molecular structure:
(1)SMILES: O(\C=C)CCO
(2)InChI: InChI=1/C4H8O2/c1-2-6-4-3-5/h2,5H,1,3-4H2
(3)InChIKey: VUIWJRYTWUGOOF-UHFFFAOYAW
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 29gm/m3 (29000mg/m3) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(11), Pg. 94, 1974. | |
mouse | LD50 | oral | 2900mg/kg (2900mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(3), Pg. 12, 1977. | |
rat | LD50 | oral | 3910mg/kg (3910mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(3), Pg. 12, 1977. |
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