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A14245 Ethoxyacetylene, ca 50% w/w in hexanes

CAS Number
927-80-0
Synonyms
Ethyl ethynyl ether

Stock No. Size Price ($) Quantity Availability
A14245-03 1g 26.90
A14245-06 5g 81.60
A14245-14 25g 311.00
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Ethoxyacetylene, ca 50% w/w in hexanes

MDL
MFCD00009247
EINECS
213-164-5

Chemical Properties

Formula
C4H6O
Formula Weight
70.09
Boiling Point
55-56°
Flash Point
-28°(-18°F)
Density
0.718
Refractive Index
1.3800
Storage & Sensitivity
Keep Cold.
Solubility
Slightly miscible with water.

Applications

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.

Notes

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-H304-H312-H315-H319-H332-H336-H351-H361f-H373

Highly flammable liquid and vapour. May be fatal if swallowed and enters airways. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. May cause drowsiness or dizziness. Suspected of causing cancer. Suspected of damaging fertility. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P280i-P281-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P312-P331-P332+P313-P337+P313-P363-P370+P37

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear eye/face protection. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician if you feel unwell. Do NOT induce vomiting. If skin irritation occurs: If eye irritation persists: Wash contaminated clothing before reuse. In case of fire:

Other References

Beilstein
741882
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2909.19
TSCA
No
RTECS
KN9900000

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