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2-(Vinyloxy)ethanol

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Name

2-(Vinyloxy)ethanol

EINECS 212-124-4
CAS No. 764-48-7 Density 0.942 g/cm3
PSA 29.46000 LogP 0.13880
Solubility N/A Melting Point N/A
Formula C4H8O2 Boiling Point 133.7 ºC at 760 mmHg
Molecular Weight 88.1063 Flash Point 50 ºC
Transport Information UN 3271 3/PG 3 Appearance N/A
Safety 16-36 Risk Codes 10
Molecular Structure Molecular Structure of 764-48-7 (2-(Vinyloxy)ethanol) Hazard Symbols N/A
Synonyms

2-Hydroxyethyl vinyl ether;Ethylene glycol vinyl ether;Hydroxyethylvinyl ether;Monovinyl glycol ether;Vinyloxyethanol;

Article Data 21

2-(Vinyloxy)ethanol Synthetic route

4360-63-8

2-bromomethyl-1,3-dioxolane

764-48-7

2-hydroxyethyl vinyl ether

Conditions
ConditionsYield
With sodium In diethyl ether for 6h; Heating;70%
107-21-1

ethylene glycol

74-86-2

acetylene

A

764-78-3

ethylene glycol divinyl ether

B

764-48-7

2-hydroxyethyl vinyl ether

Conditions
ConditionsYield
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;
107-21-1

ethylene glycol

74-86-2

acetylene

A

497-26-7

2-methyl-1,3-dioxolane

B

764-78-3

ethylene glycol divinyl ether

C

764-48-7

2-hydroxyethyl vinyl ether

Conditions
ConditionsYield
With sodium hydroxide; cesium fluoride at 138 - 142℃; under 10297.1 Torr; for 3.5h;A 4%
B 11%
C 26%
14690-04-1

2-(2-vinyloxy-ethoxy)-[1,3,2]dioxaphospholane

764-48-7

2-hydroxyethyl vinyl ether

Conditions
ConditionsYield
With potassium hydroxide
929-37-3

2-[2-(ethenyloxy)ethoxy]ethan-1-ol

A

497-26-7

2-methyl-1,3-dioxolane

B

64-17-5

ethanol

C

764-48-7

2-hydroxyethyl vinyl ether

Conditions
ConditionsYield
With potassium hydroxide at 170 - 250℃; Product distribution;
111-46-6

diethylene glycol

A

50-00-0

formaldehyd

B

64-17-5

ethanol

C

74-85-1

ethene

D

764-48-7

2-hydroxyethyl vinyl ether

E

75-07-0

acetaldehyde

Conditions
ConditionsYield
With oxygen at 400℃; for 0.333333h; Product distribution;
4360-63-8

2-bromomethyl-1,3-dioxolane

60-29-7

diethyl ether

sodium

sodium

764-48-7

2-hydroxyethyl vinyl ether

123-91-1

1,4-dioxane

A

503-30-0

trimethylene oxide

B

50-00-0

formaldehyd

C

74-85-1

ethene

D

764-48-7

2-hydroxyethyl vinyl ether

E

H2

H2

Conditions
ConditionsYield
Mechanism; Product distribution; Quantum yield; Irradiation; 185 nm vacuum-ultraviolet photolysis;
107-21-1

ethylene glycol

74-86-2

acetylene

KOH

KOH

A

764-78-3

ethylene glycol divinyl ether

B

764-48-7

2-hydroxyethyl vinyl ether

C

2-methyl-1.3-dioxolane

2-methyl-1.3-dioxolane

Conditions
ConditionsYield
at 180℃; unter Druck;
at 120℃; unter Druck;
at 120℃; unter Druck;
at 180℃; unter Druck;
bromoacetaldehyde ethylenacetal

bromoacetaldehyde ethylenacetal

764-48-7

2-hydroxyethyl vinyl ether

Conditions
ConditionsYield
With diethyl ether; sodium

2-(Vinyloxy)ethanol Consensus Reports

Glycol ether compounds are on the Community Right-To-Know List.

2-(Vinyloxy)ethanol Specification

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%.

Ethylene glycol monovinyl ether can be prepared by ethane-1,2-diol and ethyne

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.
 
Ethylene glycol monovinyl ether can be used to get 2-methyl-[1,3]dioxolane

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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