Ethoxyethyne

Base Information

• Chemical Name: Ethoxyethyne
• CAS No.: 927-80-0
• Molecular Formula: C4H6O
• Molecular Weight: 70.091
• Hs Code.: 29091990
• European Community (EC) Number: 213-164-5
• UN Number: 1993
• UNII: B8RFM34GMK
• DSSTox Substance ID: DTXSID80239114
• Nikkaji Number: J149.801K
• Wikidata: Q72471604
• Mol file: 927-80-0.mol

Synonyms:Ethoxyethyne;927-80-0;Ethoxyacetylene;ETHYL ETHYNYL ETHER;Ethyne, ethoxy-;ethynoxyethane;Ether, ethyl ethynyl;Ethynyl ethyl ether;Ethyne, ethoxy- (9CI);EINECS 213-164-5;BRN 0741882;4-01-00-02211 (Beilstein Handbook Reference);977-80-0;ethoxy-ethyne;ETHYLETHYNYLETHER;ethoxy acetylene;1-Ethoxyethyne;ethyl ethynylether;1-Ethoxyacetylene;1-Ethoxyacetylene #;B8RFM34GMK;DTXSID80239114;AMY33551;BBL102540;MFCD00009247;STL556343;AKOS005258150;LS-67833;FT-0607730;EN300-91560;A844342

Chemical Property of Ethoxyethyne

Chemical Property:

• Appearance/Colour: Clear orange to brown solution
• Vapor Pressure: 337mmHg at 25°C
• Refractive Index: n20/D 1.379
• Boiling Point: 47.4 °C at 760 mmHg
• Flash Point: 9 °C
• PSA: 9.23000
• Density: 0.802 g/cm³
• LogP: 0.61360
• Storage Temp.: −20°C
• Water Solubility.: Slightly miscible with water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 70.041864811
• Heavy Atom Count: 5
• Complexity: 47.9

Purity/Quality:

99.9% ^*data from raw suppliers

Ethoxyacetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-38-48/20-51/53-62-65-67-36/37/38-36/38
• Safety Statements: 16-36/37-61-62-45-36/37/39-26-33-29-9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC#C
• Uses: Ethoxyacetylene is used in Arens-van Dorp synthesis to prepare propargyl alcohol via reaction with ketone. In organic synthesis, it undergoes [2+2] cycloaddition reactions with ketenes to give cyclobutenone derivatives. It is also used to prepare alpha, beta-unsaturated esters from ketones by following Meyer-Schuster rearrangement.Used with N-vinylamides and triflic anhydride in a direct, three-component synthesis of pyridines. Also used to prepare α, β-unsaturated esters from ketones via a Meyer-Schuster rearrangement. Used with N-vinylamides and triflic anhydride in a direct, three-component synthesis of pyridines. Also used to prepare α,β-unsaturated esters from ketones via a Meyer-Schuster rearrangement.

Technology Process of Ethoxyethyne

There total 18 articles about Ethoxyethyne 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%

ethoxyethynyl lithium (31612-88-1) → 1-ethoxyacetylene (927-80-0)

Guidance literature:

With dinitrogen tetraoxide; In diethyl ether; at -78 ℃; Product distribution;

DOI:10.1002/hlca.200590020

Reference yield: 89.0%

cis-1-chloro-2-ethoxyethene (23679-21-2) → 1-ethoxyacetylene (927-80-0)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In Petroleum ether; at 60 ℃; for 2h;

Reference yield: 75.0%

chloroacetaldehyde diethyl acetal (621-62-5) → 1-ethoxyacetylene (927-80-0)

Guidance literature:

With ammonia; sodium; ferric nitrate; at -70 ℃;

DOI:10.1039/b413944e

upstream raw materials:

cis-1-chloro-2-ethoxyethene

(Z)-1-bromo-2-ethoxyethene

1,2-dibromoethyl ethyl ether

1-bromo-2-ethoxyethene

Downstream raw materials:

ethyl piperidine-1-propionate

ethyl 3-morpholinopropionate

5-ethoxy-3-phenylisoxazole

N,N-phthaloyl-glycin-(1-ethoxy-vinyl ester)

Refernces

Olefination of α,α′-divinyl ketones through catalytic Meyer-Schuster rearrangement

10.1021/jo101497f

Curtis J. Rieder, Karl J. Winberg, and F. G. West explores a two-step protocol for the olefination of 1,4-pentadien-3-ones to produce [3]dendralenes.The authors developed a method involving acetylide addition followed by a catalytic Meyer-Schuster rearrangement using VO(acac)2, which proved effective for ethoxyacetylene adducts. Ethoxyacetylene is used as the acetylide source in the addition step. It is highly reactive due to its cylindrical symmetry and minimal steric demand, making it an effective nucleophile for the addition to dienones. The study also investigates unexpected reactivity, including Nazarov-type electrocyclizations, during attempted rearrangements and identifies conditions to promote the desired rearrangement. The findings contribute to the field by providing a successful olefination strategy for sensitive [3]dendralenes and insights into the mechanisms of these reactions, supported by detailed experimental procedures and spectroscopic data.

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