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Sigma-Aldrich

Ethyl 3-methyl-2-oxobutyrate

97%

Synonym(s):

Ethyl dimethylpyruvate, Ketovaline ethyl ester

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About This Item

Linear Formula:
(CH3)2CHCOCOOCH2CH3
CAS Number:
20201-24-5
Molecular Weight:
144.17
Beilstein/REAXYS Number:
1756668
EC Number:
243-587-0
MDL number:
MFCD00009122
UNSPSC Code:
12352100
PubChem Substance ID:
24853067
NACRES:
NA.22

Quality Level

100

assay

97%

refractive index

n20/D 1.410 (lit.)

bp

62 °C/11 mmHg (lit.)

density

0.989 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)C(=O)C(C)C

InChI

1S/C7H12O3/c1-4-10-7(9)6(8)5(2)3/h5H,4H2,1-3H3

InChI key

CKTYYUQUWFEUCO-UHFFFAOYSA-N

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General description

Ethyl 3-methyl-2-oxobutyrate reacts with a variety of allyl halides in the presence of indium to afford hydroxy unsaturated carbonyl compounds. Conformational behaviour of ethyl 3-methyl-2-oxobutyrate was investigated using solution FTIR in combination with ab initio calculations.

Application

Ethyl 3-methyl-2-oxobutyrate was used in the synthesis of (2SR,4SR)-5(S)-(N-Boc)-amino-6-cyclohexyl-4-hydoxy-2-isopropyl hexanoic acid.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

109.4 °F - closed cup

flash_point_c

43 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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The synthesis of (2S, 4S, 5S)-5-(N-BOC)-amino-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid lactone, an hydroxyethylene dipeptide isostere precusor.
Chakravarty PK, et al.
Tetrahedron Letters, 30(4), 415-418 (1989)
Conformational isomerism of a-ketoesters. A FTIR and ab initio study.
Ferri D, et al.
J. Chem. Soc. Perkin Trans. II, 2, 221-227 (2000)
A convenient allylation of 1, n-dicarbonyl compounds using organoindium reagents.
Lee PH, et al.
Bull. Korean Chem. Soc., 22(12), 1380-1384 (2001)

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