1 -(Ethenyloxy)-butane

Base Information

• Chemical Name: 1 -(Ethenyloxy)-butane
• CAS No.: 111-34-2
• Molecular Formula: C6H12O
• Molecular Weight: 100.161
• Hs Code.: 2909199090
• European Community (EC) Number: 203-860-7
• NSC Number: 8264
• UN Number: 2352
• UNII: 321YRT7173
• DSSTox Substance ID: DTXSID5051575
• Nikkaji Number: J75.043C
• Wikidata: Q1018214
• Metabolomics Workbench ID: 132017
• ChEMBL ID: CHEMBL3561125
• Mol file: 111-34-2.mol

Synonyms:n-Butyl vinyl ether;Ether,butyl vinyl (8CI);1-(Ethenyloxy)butane;1-(Vinyloxy)butane;1-Butoxyethene;BVE;Butoxyethene;Butoxyethylene;Butane, 1-(ethenyloxy)-;NBVE;NSC 8264;Vinylbutyl ether;Vinyl n-butyl ether;

Chemical Property of 1 -(Ethenyloxy)-butane

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 55.8mmHg at 25°C
• Melting Point: -92 °C(lit.)
• Refractive Index: 1.4026
• Boiling Point: 93.6 °C at 760 mmHg
• Flash Point: 15°F
• PSA: 9.23000
• Density: 0.776 g/cm³
• LogP: 1.94660
• Water Solubility.: 3 g/L (20℃)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 100.088815002
• Heavy Atom Count: 7
• Complexity: 41.4
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F:Flammable
• Statements: R11:; R19:
• Safety Statements: S16:; S33:; S9:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Other Monomers
• Canonical SMILES: CCCCOC=C
• General Description: **1-(Ethenyloxy)-butane (n-Butyl vinyl ether, BVE)** is a vinyl ether used as a reactant in platinum(II)-catalyzed reactions with o-ethynylbenzoates to synthesize 1-acyl-4-alkoxynaphthalenes. It participates as a key substrate in [3+2] cycloaddition with platinum-containing carbonyl ylide intermediates, facilitating the formation of naphthalene derivatives under mild conditions. This highlights its utility in organic synthesis, particularly in constructing complex aromatic frameworks. **Return:** Non-Null.

Technology Process of 1 -(Ethenyloxy)-butane

There total 29 articles about 1 -(Ethenyloxy)-butane 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: 83.0%

dibutyl acetal (871-22-7) + 6,6-Dimethyloenanthsaeure (15898-92-7) → -butyl vinyl ether (111-34-2,92680-80-3)

Guidance literature:

Reference yield: 82.0%

acetylene (74-86-2,25067-58-7) + butan-1-ol (71-36-3) → -butyl vinyl ether (111-34-2,92680-80-3)

Guidance literature:

With sodium hydroxide; cesium fluoride; at 135 - 140 ℃; for 3h; under 7600 - 10640 Torr;

DOI:10.1007/s11178-005-0222-y

Reference yield: 68.0%

(2-butoxy-ethanesulfinyl)-ethene (81577-06-2) → -butyl vinyl ether (111-34-2,92680-80-3) + ethenesulfenic acid (2492-74-2)

Guidance literature:

With potassium hydroxide; at 280 - 290 ℃;

upstream raw materials:

butane, 1-(1-ethoxyethoxy)-

dibutyl acetal

1,1-dibutoxy-2-chloro-ethane

1-chloro-hexan-3-ol

Downstream raw materials:

N-vinyl-2-oxazolidone

ethyl 2-butoxycyclopropanecarboxylate

3t-butoxy-acryloyl chloride

1-(2-chloroethoxy)butane

Refernces

Synthesis of naphthalene derivatives through platinum(II)-catalyzed reaction of 2-alkynylbenzoates with vinyl ethers

10.1055/s-2007-983737

The research focuses on the development of a concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes through PtCl2-catalyzed reactions of o-ethynylbenzoates or benzothioates with vinyl ethers. The study aimed to explore an efficient methodology for synthesizing naphthalene derivatives, which are significant in organic and bioorganic chemistry, under mild conditions using simple starting materials. The researchers confirmed the presence of platinum-containing carbonyl ylides as key reactive intermediates through NMR analyses and proposed that the naphthalene derivatives were produced by a [3+2] cycloaddition of the ylide species with vinyl ethers, followed by 1,2-alkyl migration of the generated platinum-carbene intermediates. The use of various solvents, catalysts, and substrates such as isopropyl o-ethynylbenzoate, butyl vinyl ether, and [PtCl2(H2C=CH2)]2, among others, demonstrated the versatility and high yield potential of this platinum(II)-catalyzed synthesis approach. The study concluded that the concept of metal-containing 1,3-dipoles, as exemplified by the platinum(II)-containing carbonyl ylides, could find abundant application in organic chemistry, offering new opportunities for developing synthetic methods for a variety of organic molecules.