CAS 927-80-0|ethoxyethyne|ETHOXYETHYNE|ethoxy-ethyne|ETHOXYACETYLENE|Ethyl ethynyl ether|Ethoxyacetylene, 50% hexane solution|乙氧基乙炔|Ethoxyacetylene solution|Ethoxyacetylene|乙氧基乙炔溶液

General Information

Structure

Molecular Formula

C₄H₆O

Molecular Mass

70.08984

Exact Mass

70.04186481

Charge

InChI

InChI=1S/C4H6O/c1-3-5-4-2/h1H,4H2,2H3

InChIKey

WMYNMYVRWWCRPS-UHFFFAOYSA-N

Canonic Smiles

CCOC#C

Isomeric Smiles

O(CC)C#C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.6464

LogD (pH = 7.4)

0.6464

Log P

0.6464

Molar Refractivity

19.0474

Polarizability

7.6914005

Polar Surface Area

9.23

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

ethoxyethyne

Synonyms

ETHOXYETHYNEETHOXYACETYLENEEthyl ethynyl etherEthoxyacetylene, 50% hexane solution乙氧基乙炔Ethoxyacetylene solutionEthoxyacetylene乙氧基乙炔溶液

IUPAC Traditional name

ethoxy-ethyne

Names and Identifiers

Registration numbers

PubChem CID

61239

PubChem SID

1620761362485643424845309

CAS Number

Beilstein Number

MDL Number

EC Number

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

05212038

MP Biomedicals Rare Chemical collection

05214288

MP Biomedicals Rare Chemical collection

Sigma Aldrich

271365

Application
Used with N-vinylamides and triflic anhydride in a direct, three-component synthesis of pyridines.1 Also used to prepare α,β-unsaturated esters from ketones via a Meyer-Schuster rearrangement.2
Packaging
1, 5 g in glass bottle

02520

Other Notes
Lithiation and alkylation gives ethoxyalkynes, electron-rich alkynes, useful for [2+2] cycloadditions1,2,3,4

Molecule Details

References

PubChem Literature

From Data Sources

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

• 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 ɑ?-unsaturated acids. Alternatively, partial reduction of the adduct followed by hydrolysis provides a route to ɑ?-unsaturated aldehydes: J. Chem. Soc., 1823 (1949); Rec. Trav. Chim., 82, 305 (1963):

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

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity