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927-80-0 - Ethoxyacetylene, ca 50% w/w in hexanes - Ethyl ethynyl ether - A14245 - Alfa Aesar

A14245 Ethoxyacetylene, ca 50% w/w in hexanes

CAS Number
Ethyl ethynyl ether

Size Price ($) Quantity Availability
1g 25.80
5g 78.40
25g 299.00
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Ethoxyacetylene, ca 50% w/w in hexanes


Chemical Properties

Formula Weight
Boiling Point
Flash Point
Refractive Index
Slightly miscible with water.


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.


Incompatible with strong oxidizing agents and strong acids.

Literature References

Supplied in solution to reduce polymerization. Quantities offered relate to gross weight of solution.

Undergoes [2+2] cycloaddition reactions with ketenes to give cyclobutenone derivatives: J. Org. Chem., 38, 1451 (1973).

Adds to carbonyl compounds in the presence of ZnBr2: Can. J. Chem., 54, 2310 (1976).

The Grignard reagent, prepared by exchange with ethyl magnesium bromide, adds to carbonyl compounds to give carbinols which rearrange in acid to ɑß-unsaturated acids. Alternatively, partial reduction of the adduct followed by hydrolysis provides a route to ɑß-unsaturated aldehydes: J. Chem. Soc., 1823 (1949); Rec. Trav. Chim., 82, 305 (1963):

Rearrangement by BF3 etherate leads directly to the ethyl ester: Rec. Trav. Chim., 78, 664 (1959); Chem. Lett., 1129 (1981); 241, 1271 (1982). See also Chloroacetaldehyde diethyl­ acetal, L07661.

Has been used as a mild dehydrating agent in peptide synthesis: Rec. Trav. Chim., 77, 1153 (1958), and for conversion of sensitive dicarboxylic acids to their anhydrides: J. Org. Chem., 33, 3808 (1968).

Aleman, G. H. J.; Machado, R. A. R.; Gorls, H.; Baldwin, I. T.; Bolan, W. Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones. Org. Biomol. Chem. 2015, 13 (21), 5885-5893.

Henry, C.; Bolien, D.; Ibanescu, B.; Bloodworth, S.; Harrowven, D. C.; Zhang, X.; Craven, A. Generation and Trapping of Ketenes in Flow. Eur. J. Org. Chem. 2015, 2015 (7), 1491-1499.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H303-H315-H361-H373-H304

Highly flammable liquid and vapour. May be harmful if swallowed. Causes skin irritation. Suspected of damaging fertility or the unborn child. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.

Precautionary Statements: P260-P201-P280h-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves/clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Hazard Class
Packing Group
Harmonized Tariff Code


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