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Merck
CN

168092

Ethyl 2-oxocyclopentanecarboxylate

95%

Synonym(s):

2-(Ethoxycarbonyl)cyclopentanone, Ethyl cyclopentanone-2-carboxylate

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About This Item

Linear Formula:
(O=)C5H7CO2C2H5
CAS Number:
611-10-9
Molecular Weight:
156.18
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24850232
EC Number:
210-253-0
Beilstein/REAXYS Number:
387787
MDL number:
MFCD00001412

Key Documents

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Product Name

Ethyl 2-oxocyclopentanecarboxylate, 95%

InChI key

JHZPNBKZPAWCJD-UHFFFAOYSA-N

InChI

1S/C8H12O3/c1-2-11-8(10)6-4-3-5-7(6)9/h6H,2-5H2,1H3

SMILES string

CCOC(=O)C1CCCC1=O

assay

95%

refractive index

n20/D 1.452 (lit.)

bp

102-104 °C/11 mmHg (lit.)

density

1.054 g/mL at 25 °C (lit.)

functional group

ester
ketone

Quality Level

200

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Application

Ethyl 2-oxocyclopentanecarboxylate was used in stereoselective synthesis of (±)-cis,cis-spiro[4.4]nonane-1,6-diol. It was also used in the synthesis of tanikolide.

General description

Phase-transfer benzylation reaction of ethyl 2-oxocyclopentanecarboxylate with benzyl bromide in microreactor has been investigated. Ethyl 2-oxocyclopentanecarboxylate participates in cobalt (II) Schiff′s base complex catalyzed oxidation of primary and secondary alcohols.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

170.6 °F - closed cup

flash_point_c

77 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCBN4527V
BCBB1451V
BCBB1451
1382320
1330999

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A new synthesis of tanikolide.
Zhai H, et al.
Tetrahedron Letters, 44(14), 2893-2894 (2003)
Masaharu Ueno et al.
Chemical communications (Cambridge, England), (8)(8), 936-937 (2003-05-15)
Phase-transfer alkylation in a microreactor proceeds smoothly, and the reaction has been found to be more efficient than that in a round-bottomed flask with vigorous stirring; we have observed by an optical microscope study that an interfacial area provided by
Cobalt (II) Schiff's base complex catalysed oxidation of alcohols with dioxygen in the presence of ethyl 2-oxocyclopentanecarboxylate.
Punniyamurthy T and Iqbal J.
Tetrahedron Letters, 35(23), 4007-4010 (1994)
An improved synthesis and resolution of (?)-< i> cis, cis</i>-spiro [4.4] nonane-1, 6-diol.
Nieman JA, et al.
Tetrahedron Asymmetry, 4(9), 1973-1976 (1993)

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