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109-93-3

Basic Information
CAS No.: 109-93-3
Name: Divinyl ether
Article Data: 34
Molecular Structure:
Molecular Structure of 109-93-3 (Divinyl ether)
Formula: C4H6 O
Molecular Weight: 70.091
Synonyms: Vinyl ether(6CI,8CI); Divinyl ether; Divinyl oxide; Vinesthene; Vinesthesin; Vinethen;Vinethene; Vinether; Vinidyl; Vinydan
Density: 0.769g/cm3
Melting Point: 133-136?°C(lit.)
Boiling Point: 28.3°Cat760mmHg
Flash Point: °C
Hazard Symbols: Flammable, severe fire and explosion risk; explosive limits in air 1.7–27%. Toxic by inhalation, overexposure may be fatal.
Risk Codes: R36/37/38
Safety: Mildly toxic by inhalation. Mutation data reported. Prolonged exposure causes liver injury. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. A severe explosion hazard in the form of vapor when exposed to heat or flame. Forms peroxides when exposed to air or oxygen. Hypergolic reaction with concentrated nitric acid. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. Used as an inhalation anesthetic. See also ETHERS.
PSA: 9.23000
LogP: 1.29000
Synthetic route
111-44-4

3-oxa-1,5-dichloropentane

74-89-5

methylamine

A

109-02-4

4-methyl-morpholine

B

109-93-3

1,1'-oxybisethene

Conditions
ConditionsYield
With sodium hydroxide In water at 90 - 95℃; for 4h;A 50%
B 10%
111-44-4

3-oxa-1,5-dichloropentane

74-89-5

methylamine

A

123-91-1

1,4-dioxane

B

109-02-4

4-methyl-morpholine

C

109-93-3

1,1'-oxybisethene

D

110-75-8

2-chloroetyl vinyl ether

Conditions
ConditionsYield
With sodium hydroxide In water at 90 - 95℃; for 4h;A 12%
B 25%
C 20%
D 7%
764-78-3

ethylene glycol divinyl ether

109-93-3

1,1'-oxybisethene

Conditions
ConditionsYield
With potassium hydroxide at 105 - 110℃; for 5h;15%
With potassium hydroxide at 105 - 110℃; for 5h;15%
627-51-0

divinyl sulfide

109-93-3

1,1'-oxybisethene

Conditions
ConditionsYield
With silver(l) oxide
111-44-4

3-oxa-1,5-dichloropentane

110-75-8

2-chloroetyl vinyl ether

109-93-3

1,1'-oxybisethene

Conditions
ConditionsYield
With triethanolamine
111-44-4

3-oxa-1,5-dichloropentane

109-93-3

1,1'-oxybisethene

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide; tert-Amyl alcohol
With potassium hydroxide; diethylene glycol
110-75-8

2-chloroetyl vinyl ether

109-93-3

1,1'-oxybisethene

Conditions
ConditionsYield
With sodium hydroxide
56-23-5

tetrachloromethane

sodium amide

111-44-4

3-oxa-1,5-dichloropentane

109-93-3

1,1'-oxybisethene

7664-41-7

ammonia

111-44-4

3-oxa-1,5-dichloropentane

KOH

KOH

A

123-91-1

1,4-dioxane

B

109-93-3

1,1'-oxybisethene

C

75-07-0

acetaldehyde

D

110-75-8

2-chloroetyl vinyl ether

Conditions
ConditionsYield
at 200 - 280℃; weitere Prod.: Acetylen, Wasserstoff und Aethylenoxyd;
111-44-4

3-oxa-1,5-dichloropentane

sodium hydroxide

sodium hydroxide

A

123-91-1

1,4-dioxane

B

109-93-3

1,1'-oxybisethene

C

75-07-0

acetaldehyde

D

110-75-8

2-chloroetyl vinyl ether

Conditions
ConditionsYield
at 200 - 220℃;
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Chemistry

Product Name: Vinyl ether (CAS NO.109-93-3)


Molecular Formula: C4H6O
Molecular Weight: 70.08984g/mol
Mol File: 109-93-3.mol
Einecs: 203-720-5
Boiling point: 28.3 °C at 760 mmHg
Sensitive: Highly flammable
Stability: Slightly soluble in water
Surface Tension: 18.5 dyne/cm
Enthalpy of Vaporization: 26.28 kJ/mol
Vapour Pressure: 676 mmHg at 25°C
XLogP3-AA: 1.3
H-Bond Donor: 0
H-Bond Acceptor: 1
Rotatable Bond Count: 2
Topological Polar Surface Area: 9.2
Heavy Atom Count: 5
Complexity: 32.9
Covalently-Bonded Unit Count: 1

Uses

Much to the dismay of some pharmacologists, the synthesis and isolation of pure vinyl ether proved to be a difficult challenge for chemists; vinyl ether was suspected to be a nearly ideal anesthetic as its structure was the combination of an alkene and an ether. In practice, vinyl ether proved to have favorable properties that allowed its brief usage as an anesthetic; on the other hand, it left many unimpressed. Aggravated by the issue of potentially toxic degradation over long-term storage and possible hepatic toxicity, vinyl ether began to leave the operating theater. Today vinyl ether is a relic in the field of anesthesiology; however, the analytical techniques used to study its pharmacology laid the groundwork for the testing of new anesthetic agents.

Toxicity Data With Reference

1.    

mmo-sat 1 pph

    BJANAD    British Journal of Anesthesia. 51 (1979),417.
2.    

mma-sat 1 pph

    BJANAD    British Journal of Anesthesia. 51 (1979),417.
3.    

sce-ham:ovr 19,900 ppm

    ANESAV    Anesthesiology. 50 (1979),426.
4.    

ihl-mus LC50:329 g/m3/15M

    ANESAV    Anesthesiology. 11 (1950),455.

Safety Profile

Mildly toxic by inhalation. Mutation data reported. Prolonged exposure causes liver injury. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. A severe explosion hazard in the form of vapor when exposed to heat or flame. Forms peroxides when exposed to air or oxygen. Hypergolic reaction with concentrated nitric acid. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. Used as an inhalation anesthetic. See also ETHERS.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

 Vinyl ether ,its CAS NO. is 109-93-3,the synonyms is Divinyl ether ; Ethenyloxyethene ; 1,1'-Oxybisethene ; Divinyl oxide ; Vinesthesin ; Vinethene ; Vinydan .