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E35400

Sigma-Aldrich

Ethyl 2-methylacetoacetate

90%

Synonym(s):

Ethyl 2-methyl-3-oxobutanoate

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About This Item

Linear Formula:
CH3COCH(CH3)CO2C2H5
CAS Number:
609-14-3
Molecular Weight:
144.17
Beilstein:
1071742
EC Number:
210-179-9
MDL number:
MFCD00009164
UNSPSC Code:
12352100
PubChem Substance ID:
24894520
NACRES:
NA.22

Assay

90%

form

liquid

refractive index

n20/D 1.418 (lit.)

bp

187 °C (lit.)

density

1.019 g/mL at 25 °C (lit.)

SMILES string

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

InChI

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

InChI key

FNENWZWNOPCZGK-UHFFFAOYSA-N

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Application

  • Ethyl 2-methylacetoacetate is used as a substrate in the rhenium-catalyzed synthesis of multisubstituted aromatic compounds.
  • It can be employed in the synthesis of coumarin derivatives via Pechmann condensation.
  • It undergoes dehydration to yield conjugated alkynyl and allenyl esters.
  • It is also used in the total synthesis of chlorotonil A, yangjinhualine A, (+)- and (−)-saudin.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

145.4 °F - closed cup

Flash Point(C)

63 °C - closed cup

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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K Iwamoto et al.
Bioscience, biotechnology, and biochemistry, 64(1), 194-197 (2000-04-15)
Seven fungi, which are found to reduce ethyl 3-oxobutanoate in high yields, were tested for their reducing ability for ethyl 2-methyl 3-oxobutanoate. We obtained some interesting findings. In particular, Penicillium purpurogenum reduced ethyl 2-methyl 3-oxobutanoate to the corresponding alcohols with
Concise, regiocontrolled synthesis of yangjinhualine A.
Boukouvalas J and McCann L C
Tetrahedron Letters, 52(11), 1202-1204 (2011)
Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C? C Single-Bond Cleavage.
Kuninobu Y, et al.
Organic Letters, 10(14), 3133-3135 (2008)
The total synthesis of chlorotonil A.
Rahn N and Kalesse M
Angewandte Chemie (International Edition in English), 47(3), 597-599 (2008)
T Kuramoto et al.
Bioscience, biotechnology, and biochemistry, 63(3), 598-601 (1999-05-05)
Chlorella pyrenoidosa Chick reduced ethyl 2-methyl 3-oxobutanoate to the corresponding alcohols with the diastereomer (anti/syn) ratio of 53/47. The enantiomer excesses of anti-(2S, 3S)- and syn-(2S, 3R)-hydroxy esters were 89 and > 99ee% respectively. C. vulgaris and C. regularis afforded
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