Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

E35400

Sigma-Aldrich

Ethyl 2-methylacetoacetate

90%

Synonym(s):

Ethyl 2-methyl-3-oxobutanoate

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
STBJ7467
STBH5996
STBG3016V
STBB6234V
STBC4296V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Selective One-Pot Synthesis of Allenyl and Alkynyl Esters from β-Ketoesters.
Maity P and Lepore S D
The Journal of Organic Chemistry, 74(1), 158-162 (2008)
The total synthesis of chlorotonil A.
Rahn N and Kalesse M
Angewandte Chemie (International Edition in English), 47(3), 597-599 (2008)
Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C? C Single-Bond Cleavage.
Kuninobu Y, et al.
Organic Letters, 10(14), 3133-3135 (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
Synthesis of coumarins catalyzed by eco-friendly W/ZrO2 solid acid catalyst.
Reddy B M, et al.
Synthetic Communications, 31(23), 3603-3607 (2001)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service