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Sigma-Aldrich

3-Ethoxy-2-cyclopentenone

98%

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About This Item

Linear Formula:
C2H5OC5H5(=O)
CAS Number:
22627-70-9
Molecular Weight:
126.15
Beilstein:
2041482
EC Number:
245-138-4
MDL number:
MFCD00042963
UNSPSC Code:
12352100
PubChem Substance ID:
24864500
NACRES:
NA.22

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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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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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2-Cyclopenten-1-one 98%

Sigma-Aldrich

C112909

2-Cyclopenten-1-one

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
596144
CorpBase ID (for auto-filling citation data) null
Palladium-catalyzed rearrangements of 2-cyclopentenyloxypyrimidines in the preparation of pyrimidine carbonucleosides.
Falck-Pedersen ML, et al.
Acta Chemica Scandinavica, 47, 72-72 (1993)
An efficient synthesis of 3-aminocyclopent-2-en-1-one.
Kikani BB, et al.
Synthesis, 2, 176-176 (1991)

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