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29780

Sigma-Aldrich

Ethyl 2-oxocyclopentanecarboxylate

purum, ≥97.0% (GC)

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
Beilstein:
387787
EC Number:
210-253-0
MDL number:
MFCD00001412
UNSPSC Code:
12352100
PubChem Substance ID:
329753390

grade

purum

Assay

≥97.0% (GC)

refractive index

n20/D 1.452 (lit.)
n20/D 1.453

bp

102-104 °C/11 mmHg (lit.)

density

1.054 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)C1CCCC1=O

InChI

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

InChI key

JHZPNBKZPAWCJD-UHFFFAOYSA-N

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General description

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

Application

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

170.6 °F - closed cup

Flash Point(C)

77 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

29780-VAR:
29780-100ML:
29780-500ML:
29780-25ML:
29780-BULK:
29780-INTR:

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Certificates of Analysis (COA)

Lot/Batch Number
1204823
017054/1
1382320
1330999
016459/1

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A new synthesis of tanikolide.
Zhai H, et al.
Tetrahedron Letters, 44(14), 2893-2894 (2003)
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)
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)

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