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393037

Sigma-Aldrich

3-Ethoxy-2-cyclopentenone

98%

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Linear Formula:
C2H5OC5H5(=O)
CAS Number:
Molecular Weight:
126.15
Beilstein/REAXYS Number:
2041482
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

liquid

refractive index

n20/D 1.492 (lit.)

bp

60-63 °C/0.3 mmHg (lit.)

density

1.062 g/mL at 25 °C (lit.)

SMILES string

CCOC1=CC(=O)CC1

InChI

1S/C7H10O2/c1-2-9-7-4-3-6(8)5-7/h5H,2-4H2,1H3

InChI key

SUQNVCCJLBQVEI-UHFFFAOYSA-N

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1 of 4

This Item
C112402359475393274
3-Ethoxy-2-cyclopentenone 98%

393037

3-Ethoxy-2-cyclopentenone

Cyclopentanone ReagentPlus®, ≥99%

C112402

Cyclopentanone

3-Methoxy-2-cyclopenten-1-one 99%

393274

3-Methoxy-2-cyclopenten-1-one

density

1.062 g/mL at 25 °C (lit.)

density

0.951 g/mL at 25 °C (lit.)

density

-

density

-

refractive index

n20/D 1.492 (lit.)

refractive index

n20/D 1.437 (lit.)

refractive index

-

refractive index

-

form

liquid

form

liquid

form

powder

form

solid

bp

60-63 °C/0.3 mmHg (lit.)

bp

130-131 °C (lit.)

bp

146-148 °C/0.75 mmHg (lit.)

bp

-

General description

3-Ethoxy-2-cyclopentenone (3-Ethoxy-2-cyclopenten-1-one, 3-Ethoxycyclopentenone) is a cyclic β-alkoxy α,β-unsaturated ketone. Its manganese(III) acetate based tandem oxidation has been investigated. Its various physical properties such as density, refractive index and boiling point have been reported.

Application

3-Ethoxy-2-cyclopentenone (3-Ethoxy-2-cyclopenten-1-one) may be used as a starting material in the synthesis of the following:
  • allylic cyclopentenyl alcohols like 2-cyclopentenol, 3-methyl-2-cyclopentenol and 3-methoxymethaoxymethyl-2-cyclopentenol
  • 3-aminocyclopent-2-en-1-one
  • (E)-5-(((2S*,3S*)-3-((benzyloxy)methyl)oxiran-2- yl)methylene)-3-ethoxycyclopent-2-enone, an γ,δ -epoxy-α,β-unsaturated cyclic enone

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves


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Manganese (III) acetate based tandem oxidation of various α and β-alkoxy α, β-unsaturated ketones.
Tanyeli C, et al.
Tetrahedron, 58(50), 9983-9988 (2002)
Fumihiko Yoshimura et al.
Organic & biomolecular chemistry, 10(28), 5431-5442 (2012-06-19)
We developed a new method for stereoselective construction of an all-carbon quaternary stereogenic center on a carbocyclic ring based on regio- and stereoselective S(N)2' alkylation reactions of γ,δ-epoxy-α,β-unsaturated cyclic ketones. Treatment of the ketones, which were readily prepared in enantiomerically
An efficient synthesis of 3-aminocyclopent-2-en-1-one.
Kikani BB, et al.
Synthesis, 2, 176-176 (1991)
Palladium-catalyzed rearrangements of 2-cyclopentenyloxypyrimidines in the preparation of pyrimidine carbonucleosides.
Falck-Pedersen ML, et al.
Acta Chemica Scandinavica, 47, 72-72 (1993)
596144
CorpBase ID (for auto-filling citation data) null

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