Allyl vinyl ether

Base Information

• Chemical Name: Allyl vinyl ether
• CAS No.: 3917-15-5
• Molecular Formula: C5H8 O
• Molecular Weight: 84.1179
• Hs Code.: 2909199090
• European Community (EC) Number: 223-482-6
• NSC Number: 6270
• UNII: FJ2J0N55CS
• DSSTox Substance ID: DTXSID70192406
• Nikkaji Number: J92.983B
• Wikidata: Q27278012
• Mol file: 3917-15-5.mol

Synonyms:Allyl vinyl ether;3917-15-5;Ether, allyl vinyl;Vinyl allyl ether;1-Propene, 3-(ethenyloxy)-;3-ethenoxyprop-1-ene;Allyl ethenyl ether;3-ethenoxy-1-propene;3-(Ethenyloxy)propene;NSC 6270;EINECS 223-482-6;UNII-FJ2J0N55CS;BRN 1697665;FJ2J0N55CS;AI3-25058;NSC-6270;4-01-00-02085 (Beilstein Handbook Reference);3-(vinyloxy)prop-1-ene;3-(ethenyloxy)prop-1-ene;3-(Vinyloxy)-1-propene #;WLN: 1U2O1U1;DTXSID70192406;NSC6270;MFCD00039827;AKOS006230173;LS-67716;FT-0622017;A829326;Q27278012;Allyl vinyl ether, 95% stab. with 0.1% potassium hydroxide

Chemical Property of Allyl vinyl ether

Chemical Property:

• Vapor Pressure: 103mmHg at 25°C
• Melting Point: 240?°C (dec.)(lit.)
• Refractive Index: 1.4140
• Boiling Point: 78.4 °C at 760 mmHg
• Flash Point: <-55.6
• PSA: 9.23000
• Density: 0.781 g/cm³
• LogP: 1.33250
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 84.057514874
• Heavy Atom Count: 6
• Complexity: 47.9

Purity/Quality:

97% ^*data from raw suppliers

Allyl vinyl ether, 95% stab. with 0.1% potassium hydroxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R11:Highly flammable.; R22:Harmful if swallowed.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R11:Highly flammable.; R22:Harmful if swallowed.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 11-22-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC=C
• Uses: Allyl vinyl ether is used as a intermediate in chemical research.

Technology Process of Allyl vinyl ether

There total 27 articles about Allyl vinyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

S-(2-allyloxyethyl)-S-phenyl-N-tosylsulfilimine → allyl vinyl ether (3917-15-5)

Guidance literature:

at 110 - 120 ℃; for 0.5h; under 50 Torr;

Reference yield: 86.0%

glycidyl vinyl ether (3678-15-7) → allyl vinyl ether (3917-15-5)

Guidance literature:

With sodium iodide; tin(ll) chloride; In ethanol; for 0.05h; Reflux; Green chemistry;

DOI:10.1055/s-0034-1378821

Reference yield: 82.0%

allyl alcohol (107-18-6) + acetylene (74-86-2,25067-58-7) → allyl vinyl ether (3917-15-5)

Guidance literature:

With sodium hydroxide; sodium acetate; In dimethyl sulfoxide; at 80 ℃; for 4h; under 9120 Torr;

upstream raw materials:

2-(allyloxy)ethyl bromide

potassium tert-butylate

acetaldehyde diallyl acetal

acetaldehyde-(allyl-phenyl-acetal)

Downstream raw materials:

Acetylenedicarboxylic acid

4-pentenal

N-((Z)-3-Allyloxy-acryloyl)-benzamide

(1S,4S,5R)-5-Allyloxy-7-oxo-2,3-diphenyl-bicyclo[2.2.1]hept-2-ene-1,4-dicarboxylic acid dimethyl ester

Refernces

Enantioselective activation of ethers by chiral organoaluminum reagents: Application to asymmetric Claisen rearrangement

10.1016/S0957-4166(00)86119-4

The research focuses on the enantioselective activation of ethers using chiral organoaluminum reagents, specifically applying this method to asymmetric Claisen rearrangement. The purpose of the study was to develop a facile asymmetric synthesis of various acylsilanes and acylgermanes with high optical purity. The researchers found that among the various trialkylsilyl substituents of the chiral organoaluminum reagent, the more bulky t-butyldiphenylsilyl group exhibited the highest enantioselectivity. The study concluded that the chiral organoaluminum reagent could discriminate between two possible chairlike transition-state structures, leading to the formation of enantiomers with high enantiomeric excess. Key chemicals used in the process included allylic vinyl ethers, chiral organoaluminum reagents such as (R)-1 and (S)-1, and various trialkylsilyl substituents. The researchers also utilized acylsilanes and acylgermanes, which are valuable compounds in organic synthesis, and demonstrated that their method could provide a general synthesis route for these compounds with high stereoselectivity.

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