All Photos(1)
Synonym(s):
Ethyl 2-methyl-3-oxobutanoate
Linear Formula:
CH3COCH(CH3)CO2C2H5
CAS Number:
Molecular Weight:
144.17
Beilstein:
1071742
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Find documentation for the products that you have recently purchased in the Document Library.
Synthesis of coumarins catalyzed by eco-friendly W/ZrO2 solid acid catalyst.
Reddy B M, et al.
Synthetic Communications, 31(23), 3603-3607 (2001)
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)
Concise, regiocontrolled synthesis of yangjinhualine A.
Boukouvalas J and McCann L C
Tetrahedron Letters, 52(11), 1202-1204 (2011)
An enantioselective total synthesis of (+)-and (−)-saudin. Determination of the absolute configuration.
Boeckman R K, et al.
Journal of the American Chemical Society, 124(2), 190-191 (2002)
Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C? C Single-Bond Cleavage.
Kuninobu Y, et al.
Organic Letters, 10(14), 3133-3135 (2008)
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