Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 1.5h; | 92% |
With sodium ethanolate at 145 - 165℃; | |
With zinc(II) oxide at 310℃; |
ethanol
vinyltriethylsilane
A
hexaethyl disiloxane
B
ethyl vinyl ether
Conditions | Yield |
---|---|
With bromine for 4h; | A 25% B 55% |
1-phenyl-4-ethoxy-2,3-dimethylthiobutanone
A
2,4,4-Trimethyl-3-phenyl-tetrahydro-pyran-3-thiol
B
4-Ethoxy-2,2-dimethyl-1-phenyl-cyclobutanethiol
C
ethyl vinyl ether
Conditions | Yield |
---|---|
In benzene for 40h; Ambient temperature; Irradiation; through pyrex; | A 40% B 48% C n/a |
With dimethylglyoxal In benzene Quantum yield; Rate constant; Ambient temperature; Irradiation; var. senzitizers and conc. of ones; sev. solvents of different polarities; |
2,3-cis-epoxybutane
A
2-hydroxy-3-butene
B
ethene
C
isobutyraldehyde
D
ethyl vinyl ether
E
butanone
2,3-trans-epoxybutane
Conditions | Yield |
---|---|
at 757.9℃; Mechanism; Product distribution; Kinetics; reflected shocks in a pressurized driver single-pulse shock tube ; the temperature range: 900-1150 K.; | A 2.62% B 2.21% C 4.58% D 0.902% E 13.39% F 5.64% |
Conditions | Yield |
---|---|
(CO)4(palladium)4(acetate)4 for 2h; Product distribution; effect of the catalyst to the production and the selectivity; | A 9% B n/a |
tetrachloromethane
2-Bromoethyl ethyl ether
A
3,6,9-trioxaundecane
B
ethyl vinyl ether
diethyl acetal
A
ethanol
B
ethene
C
acetaldehyde
D
ethyl vinyl ether
Conditions | Yield |
---|---|
at 389 - 453℃; Kinetics; Pr.5: Kohlenmonoxid; Pr.6: Methan.Pyrolysis; |
Conditions | Yield |
---|---|
With sulfuric acid at 350℃; | |
With sodium hydrogen sulfate | |
With platinum at 280 - 290℃; |
Conditions | Yield |
---|---|
at 250℃; | |
at 300 - 500℃; in Gegenwart von Katalysatoren; |
Conditions | Yield |
---|---|
With mercury(II) diacetate | |
With sodium hydroxide; kieselguhr at 310 - 320℃; |
Conditions | Yield |
---|---|
With pyridine at 25℃; |
Conditions | Yield |
---|---|
With sodium hydroxide | |
With potassium hydroxide at 110 - 120℃; |
Conditions | Yield |
---|---|
With alkali hydroxide |
Conditions | Yield |
---|---|
at 100 - 120℃; | |
unter Druck; reagiert analog mit anderen Alkoholaten; |
3-ethoxy-2,2-diphenylcyclobutanone
A
diphenyl ketene
B
ethyl vinyl ether
Conditions | Yield |
---|---|
bei gelindem Erwaermen oder laengerem Aufbewahren; |
Conditions | Yield |
---|---|
at 100℃; unter Druck; |
Conditions | Yield |
---|---|
With magnesium at 100 - 110℃; |
Conditions | Yield |
---|---|
With sulfuric acid; mercury(II) sulfate Behandeln des entstandenen Reaktionsgemisch mit Alkohol; |
Conditions | Yield |
---|---|
With sodium at 130 - 140℃; | |
With diethyl ether; sodium at 0 - 20℃; |
Conditions | Yield |
---|---|
With pyridine at 120℃; | |
With potassium tert-butylate Kinetics; |
Conditions | Yield |
---|---|
In various solvent(s) Product distribution; Irradiation; infrared multiphoton induced photolysis; the luminescence of the reaction mixture was also investigated; | |
Irradiation; luminescence during the photodecompsition; |
Conditions | Yield |
---|---|
In various solvent(s) Product distribution; Irradiation; infrared multiphoton induced photolysis; the luminescence of the reaction mixture was also investigated; | |
Irradiation; luminescence during the photodecompsition; |
monoethylene glycol diethyl ether
A
ethoxyacetaldehyde
B
1,2-diethoxyethylene
C
(2R,3R,4S,6R)-3,5-Diethoxy-6-ethoxymethyl-tetrahydro-pyran-2,4-diol
2,4-di-O-ethylthreose
E
ethyl vinyl ether
Conditions | Yield |
---|---|
Rhodium(I) compound In chloroform-d1 for 72h; Product distribution; |
acetaldehyde ethyl 1-propenyl acetal
A
propionaldehyde
B
ethyl vinyl ether
Conditions | Yield |
---|---|
(Ph3P)CH3COPdCl2 In dichloromethane Product distribution; Ambient temperature; |
propargyl alcohol
ethyl vinyl ether
acetaldehyde ethyl propargyl acetal
Conditions | Yield |
---|---|
With trifluoroacetic acid Inert atmosphere; | 100% |
With trifluoroacetic acid at 20 - 60℃; for 0.333333h; | 100% |
With toluene-4-sulfonic acid at 0 - 15℃; | 92% |
tetrachloromethane
ethyl vinyl ether
Ethyl-(1,3,3,3-tetrachlor-propyl)-ether
Conditions | Yield |
---|---|
With dibenzoyl peroxide | 100% |
With dibenzoyl peroxide for 2h; Heating; | 90.3% |
With pyridine; dibenzoyl peroxide |
ethyl vinyl ether
2-methyl-but-3-yn-2-ol
2-methyl-3-butyn-2-ol 1-ethoxyethyl ether
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1h; | 100% |
With sulfuric acid for 0.5h; | 77% |
With hydrogenchloride |
(S)-Ethyl lactate
ethyl vinyl ether
(2S,1'R/S)-Ethyl-2-(1'-ethoxyethoxy)propanoate
Conditions | Yield |
---|---|
toluene-4-sulfonic acid | 100% |
With toluene-4-sulfonic acid at -20℃; for 0.75h; | 98% |
With pyridinium p-toluenesulfonate In dichloromethane 1.) 0 deg C, 50 min, 2.) 1 h, room temp.; | 97% |
vanillin
ethyl vinyl ether
3-methoxy-4-(ethoxyethylidene-oxy)-benzaldehyde
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In tetrahydrofuran at 20℃; for 30h; Etherification; | 100% |
With pyridinium p-toluenesulfonate; sodium hydrogencarbonate In dichloromethane for 6h; Ambient temperature; | 90% |
With pyridinium p-toluenesulfonate In dichloromethane |
4-nitrobenzenesulfenyl chloride
ethyl vinyl ether
p-nitrophenyl 2-ethoxy-2-chloroethyl sulfide
Conditions | Yield |
---|---|
In benzene at 20℃; for 0.5h; | 100% |
Ethyl (R)-3-hydroxybutanoate
ethyl vinyl ether
Conditions | Yield |
---|---|
trifluoroacetic acid | 100% |
dimethyl (S)-malate
ethyl vinyl ether
(S)-(-)-dimethyl 2-O-(1-ethoxyethyl)malate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 36h; | 100% |
With trifluoroacetic acid for 48h; Ambient temperature; Yield given; |
Diethyl (S)-malate
ethyl vinyl ether
(S)-(-)-Aepfelsaeurediaethylester α-Aethoxyaethylaether
Conditions | Yield |
---|---|
With trifluoroacetic acid at 20℃; for 120h; | 100% |
With trifluoroacetic acid for 48h; Ambient temperature; | 98.8% |
With hydrogenchloride; silver 1) 0 deg C to r.t., overnight, 2) 1 h; | 92.8% |
3-chloro-2-hydroxy-1-propyl acetate
ethyl vinyl ether
3-Chloro-2-(1-ethoxyethoxy)-1-propyl acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 35 - 45℃; for 20h; | 100% |
With toluene-4-sulfonic acid at 35 - 40℃; for 18h; | |
With pyridinium p-toluenesulfonate In dichloromethane | 44.0 g (98.0%) |
3-hydroxy-3-methyl-1-cyano-1-butyne
ethyl vinyl ether
3-methyl-3-(α-ethoxyethoxy)-1-cyano-1-butyne
Conditions | Yield |
---|---|
With trifluoroacetic acid at 20 - 25℃; | 100% |
With hydrogenchloride at 30℃; for 3h; | 65% |
3-hydroxylbutyl benzoate
ethyl vinyl ether
Benzoesaeure-<3-(1'-aethoxyaethoxy)-butyl>ester
Conditions | Yield |
---|---|
With trifluoroacetic acid for 48h; Ambient temperature; | 100% |
4-(2-Hydroxyethyl)-<2.2>paracyclophan
ethyl vinyl ether
1-(<2.2>Paracyclophan-4-ethoxy)-1-ethoxy-ethan
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane for 5h; Ambient temperature; | 100% |
rac-methyl(1-naphthyl)phenylchlorosilane
ethyl vinyl ether
(1-ethoxyethenyl)methyl(naphth-1-yl)phenylsilane
Conditions | Yield |
---|---|
With tert.-butyl lithium In tetrahydrofuran; pentane 1) -78 to 23 deg C 2) 23 deg C, 30 min; | 100% |
(1S*,2R*,3R*)-2,6,6-Trimethylbicyclo<3.1.1>heptan-3-ol
ethyl vinyl ether
(1S*,2R*,3R*)-3-(1-ethoxyethoxy)-2,6,6-trimethylbicyclo<3.1.1>heptane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 0.666667h; Ambient temperature; | 100% |
<3aα,4α,5β,6aα>-(+/-)-hexahydro-5-hydroxy-4-<(E)-4-(3-chlorophenoxy)-(3α)-hydroxy-1-butenyl>-2H-cyclopentafuran-2-one
ethyl vinyl ether
(1SR,5RS,6RS,7RS)-6-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-7-(1-ethoxy-ethoxy)-2-oxabicyclo<3.3.0>octan-3-one
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 0.5h; | 100% |
(+)-(R)-2-cyclopentene-1-ol
ethyl vinyl ether
1-(1-ethoxy-2-bromoethoxy)-2-cyclopentene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane 1) -40 to -50 deg C, 2h, 2) RT, 16h; | 100% |
1-(3-methoxyphenyl)-1,2-ethanediol
ethyl vinyl ether
1-ethoxyethyl 2-methoxy-2-(3-methoxyphenyl)ethyl ether
Conditions | Yield |
---|---|
With trifluoroacetic acid | 100% |
(4R*,4aS*,8aR*)-4,4a,5,8-Tetrahydro-4-hydroxy-4a-methoxycarbonyl-1(8aH)-naphthalenone
ethyl vinyl ether
(4R*,4aS*,8aR*)-4-(1-Ethoxy)ethoxy-4,4a,5,8-tetrahydro-4a-methoxycarbonyl-1(8aH)-naphthalenone
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 6h; Ambient temperature; | 100% |
pyridinium p-toluenesulfonate In dichloromethane Ambient temperature; Yield given; |
(S)-(-)-hydroxy-2 octanoate d'ethyle
ethyl vinyl ether
ethyl-2-(1-ethoxyethoxy)octanoate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 1h; Ambient temperature; | 100% |
(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
ethyl vinyl ether
(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
Conditions | Yield |
---|---|
With hydrogen cation | 100% |
In tetrahydrofuran at 0℃; for 2h; | 100% |
With toluene-4-sulfonic acid In tetrahydrofuran for 0.5h; | 95% |
With methanesulfonic acid In tetrahydrofuran at 0℃; |
2-(2-methoxyethoxy)-2-(3-methoxyphenyl)ethanol
ethyl vinyl ether
1-ethoxyethyl 2-(2-methoxyethoxy)-2-(3-methoxyphenyl)ethyl ether
Conditions | Yield |
---|---|
With trifluoroacetic acid | 100% |
N-(2',4'-dichloro-6'-oxo-2',4'-cyclohexadien-1'-ylidene)-4-nitrobenzamide
ethyl vinyl ether
(5,7-Dichloro-2-ethoxy-2,3-dihydro-benzo[1,4]oxazin-4-yl)-(4-nitro-phenyl)-methanone
Conditions | Yield |
---|---|
In acetone at 20℃; Product distribution; Kinetics; Thermodynamic data; rate constants in various solvents, in benzene and 1,4-dioxane at different temperatures, ΔH(excit.), ΔS(excit.); | 100% |
2-(1-acetyl-2-oxoindolin-3-ylidene)1,3-indandione
ethyl vinyl ether
spiro<2,3,4,5-tetrahydro-2-ethoxy-5-ketoindano<1,2-b>pyran-4-3'(1'-acetyl-2'-oxo)indoline>
Conditions | Yield |
---|---|
at 100℃; for 2h; Paar bomb; | 100% |
1,3,4,4a,7,8,8a,9-octahydro-8aβ-hydroxymethyl-1α,4aβ-dimethyl-2,6-phenanthrenedione 2-(ethylene acetal)
ethyl vinyl ether
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 1h; Ambient temperature; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane |
1-acetyl-2-oxoindolin-3-ylidene diethylmalonate
ethyl vinyl ether
2-ethoxy-4,4-dicarbethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
Conditions | Yield |
---|---|
In acetonitrile for 336h; Ambient temperature; | 100% |
4α-hydroxy-1β-methylcyclohex-2-enecarbaldehyde
ethyl vinyl ether
(1S,4R)-4-(1-Ethoxy-ethoxy)-1-methyl-cyclohex-2-enecarbaldehyde
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid a) 0 deg C, 45 min, b) 0 deg C to RT, 2 h; | 100% |
4-Hydroxymethyl-2-oxo-imidazolidine-1-carboxylic acid benzyl ester
ethyl vinyl ether
4-(1-Ethoxy-ethoxymethyl)-2-oxo-imidazolidine-1-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
With trichloroacetic acid In 1,2-dimethoxyethane at 0℃; for 4h; | 100% |
trans-6-benzyl-3-methyl-2-cyclohexen-1-ol
ethyl vinyl ether
trans-4-benzyl-3-<(ξ)-1-ethoxy-2-iodoethoxy>-1-methylcyclohexene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane at -40℃; | 100% |
2-<(R)-7-Hydroxyoctyl>-1,3-dithian
ethyl vinyl ether
2-<(R)-7-(2-Ethoxyethyl)octyl>-1,3-dithian
Conditions | Yield |
---|---|
With trifluoroacetic acid at 0℃; for 48h; | 100% |
Structure of Ethyl vinyl ether (CAS NO.109-92-2):
IUPAC Name: ethoxyethene
Empirical Formula: C4H8O
Molecular Weight: 72.1057
EINECS: 203-718-4
Index of Refraction: 1.376
Molar Refractivity: 22.05 cm3
Molar Volume: 96 cm3
Polarizability: 8.74×10-24cm3
Surface Tension: 18.8 dyne/cm
Density: 0.751 g/cm3
Enthalpy of Vaporization: 26.63 kJ/mol
Melting Point: −116 °C(lit.)
Boiling Point: 32.5 °C at 760 mmHg
Vapour Pressure: 581 mmHg at 25°C
Water Solubility: 7.8 g/L (25 ºC)
Physical Appearance: colourless liquid with an ether-like odour
Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents. May form peroxides in storage - check for their formation before use.
Product Categories: Pharmaceutical Intermediates
In medicine, Ethyl vinyl ether (CAS NO.109-92-2) is used as anesthetics, analgesics, but also as intermediates for fine chemical, intermediates for sulfadiazine. It makes up the monomer of copolymer, organic synthetic materials, spices amd lubricating oil additives.
Ethyl vinyl ether (CAS NO.109-92-2) was produced by the pressurized reaction of acetylene and ethanol in the presence of potassium hydroxide catalyst.
1. | skn-rbt 500 mg open MLD | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 11/15 ,1971. | ||
2. | sce-ham:ovr 17,900 ppm | ANESAV Anesthesiology. 50 (1979),426. | ||
3. | orl-rat LD50:6153 mg/kg | AIHAAP American Industrial Hygiene Association Journal. 30 (1969),470. |
Reported in EPA TSCA Inventory.
Hazard Codes: F+,Xi,F
Risk Statements: 12-19-36/37/38
R12:Extremely flammable.
R19:May form explosive peroxides.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-23-26-3/7-33-36
S16:Keep away from sources of ignition.
S23:Do not breathe vapour.
S3:Keep in a cool place.
S7:Keep container tightly closed.
S33:Take precautionary measures against static discharges.
S36:Wear suitable protective clothing.
RIDADR: UN 1302 3/PG 1
WGK Germany: 1
RTECS: KO0710000
F: 19
HazardClass: 3
PackingGroup: I
HS Code: 29091900
Mildly toxic by ingestion. Mutation data reported. A skin irritant. A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, foam, CO2, dry chemical. Explosive polymerization is catalyzed by methane sulfonic acid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.
DOT Classification: 3; Label: Flammable Liquid
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