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Isobutyl vinyl ether
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  • Name Isobutyl vinyl ether
  • EINECS203-678-8
  • CAS No. 109-53-5
  • Density0.773 g/cm3
  • PSA9.23000
  • LogP1.80250
  • SolubilityInsoluble (soluble in alcohol and ether)
  • Melting Point-112 °C
  • FormulaC6H12O
  • Boiling Point83 °C at 760 mmHg
  • Molecular Weight100.161
  • Flash Point8°F
  • Transport InformationUN 1304 3/PG 2
  • Appearanceclear colourless liquid
  • Safety16-23-24/25-33-37
  • Risk Codes11-38
  • Molecular Structure
    Molecular Structure of 109-53-5 (Isobutyl vinyl ether)
  • Hazard SymbolsFlammableF,IrritantXi
  • SynonymsFlammableF,IrritantXi
  • Article Data17

Isobutyl vinyl ether Synthetic route

78-83-1

2-methyl-propan-1-ol

74-86-2

acetylene

109-53-5

isobutyl vinyl ether

Conditions
ConditionsYield
With sodium hydroxide; cesium fluoride at 135 - 140℃; under 7600 - 10640 Torr; for 2h;82%
With potassium hydroxide at 135 - 155℃;
at 140℃; under 4500.45 Torr;
5669-09-0

1,1-bis(isobutyloxy)-ethane

109-53-5

isobutyl vinyl ether

Conditions
ConditionsYield
With sodium hydrogen sulfate
With quinoline; phosphorus pentoxide
19865-33-9

α-chloroethyl isobutyl ether

109-53-5

isobutyl vinyl ether

Conditions
ConditionsYield
With pyridine
13259-29-5

sodium isobutoxide

74-86-2

acetylene

109-53-5

isobutyl vinyl ether

Conditions
ConditionsYield
With N,N-diethylaniline at 185 - 190℃;
74-86-2

acetylene

isobutal alcohol

isobutal alcohol

109-53-5

isobutyl vinyl ether

Conditions
ConditionsYield
With zinc diacetate at 210 - 220℃;
With copper(I) monacetylide at 210 - 220℃;
78-83-1

2-methyl-propan-1-ol

75-07-0

acetaldehyde

109-53-5

isobutyl vinyl ether

Conditions
ConditionsYield
Stage #1: 2-methyl-propan-1-ol; acetaldehyde With hydrogenchloride In dibutyl ether at 10 - 15℃;
Stage #2: With 3-Methylpyridine In dibutyl ether at 50℃; for 1h;
78-83-1

2-methyl-propan-1-ol

75-20-7

calcium carbide

109-53-5

isobutyl vinyl ether

Conditions
ConditionsYield
With potassium fluoride; water; potassium hydroxide In neat (no solvent) at 160℃; for 13h; Temperature; Autoclave;75.8 %Spectr.
109-53-5

isobutyl vinyl ether

59938-06-6

(E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one

1214317-50-6

4-Ethoxy-2-isobutoxy-6-trifluoromethyl-3,4-dihydro-2H-pyran

Conditions
ConditionsYield
With hydroquinone at 80℃; for 30h;100%
109-53-5

isobutyl vinyl ether

isobutoxyacryloyl chloride

Conditions
ConditionsYield
In phosgene100%
109-53-5

isobutyl vinyl ether

3,3-(ethylene-dioxy)-17β-cyano-17α-hydroxy-19-norpregna-5(10),9(11)-diene

17α-[(±)1-(1-isobutyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 4h; Cooling; Large scale;100%

Isobutyl vinyl ether Chemical Properties

IUPAC Name: 1-ethenoxy-2-methylpropane 
Empirical Formula: C6H12O
Molecular Weight: 100.1589g/mol
Structure of Propane,1-(ethenyloxy)-2-methyl- (CAS NO.109-53-5):

EINECS: 203-678-8
Index of Refraction: 1.398 
Molar Refractivity: 31.27 cm3 
Molar Volume: 129.4 cm3 
Polarizability: 12.39×10-24 cm3 
Surface Tension: 20.9 dyne/cm 
Density: 0.773 g/cm3 
vapor density  3.45 (vs air)
Melting point: -112 °C
Boiling Point: 83 °C at 760 mmHg 
Enthalpy of Vaporization: 31.01 kJ/mol 
Vapour Pressure: 85.6 mmHg at 25°C 
storage temp.: Flammables area
Water Solubility: 0.7 g/L (25 oC) 
Canonical SMILES: CC(C)COC=C
InChI: InChI=1S/C6H12O/c1-4-7-5-6(2)3/h4,6H,1,5H2,2-3H3
InChIKey: OZCMOJQQLBXBKI-UHFFFAOYSA-N

Isobutyl vinyl ether Toxicity Data With Reference

1.    

orl-rat LD50:17 g/kg

     AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
2.    

ihl-rat LCLo:16,000 ppm/4H

     AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
3.    

skn-rbt LD50:20 g/kg

     AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.

Isobutyl vinyl ether Consensus Reports

Reported in EPA TSCA Inventory.

Isobutyl vinyl ether Safety Profile

Very mildly toxic by ingestion, inhalation, and skin contact. A very dangerous fire hazard when exposed to heat, flame, oxidizers. Severe explosion hazard when exposed to sparks or open flame. Can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and fumes. To fight fire, use alcohol foam, CO2, dry chemical. See also ETHERS.
Hazard Codes: FlammableF,IrritantXi
Risk Statements: 11-38
R11:Highly flammable. 
R38:Irritating to skin.
Safety Statements: 16-23-24/25-33-37
S16:Keep away from sources of ignition. 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes. 
S33:Take precautionary measures against static discharges. 
S37:Wear suitable gloves.
RIDADR: UN 1304 3/PG 2
WGK Germany: 1
RTECS: KO1300000
F: 9
HazardClass: 3.1
PackingGroup: II

Isobutyl vinyl ether Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Isobutyl vinyl ether Specification

  Propane,1-(ethenyloxy)-2-methyl- , its cas register number is 64058-30-6. It also can be called 2-Methyl-1-vinyloxypropane ; 4-01-00-02054 (Beilstein Handbook Reference) ; AI3-18425 ; IVE ; Isobutanol vinyl ether ; Isobutoxyethene ; Isobutyl vinyl ether ; Lutanol LR 8500 ; NSC 8265 ; Vinyl isobutyl ether . 
 Propane,1-(ethenyloxy)-2-methyl- (CAS NO.109-53-5) is a clear colourless liquid.

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