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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/REAXYS Number:
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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

145.4 °F - closed cup

flash_point_c

63 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Concise, regiocontrolled synthesis of yangjinhualine A.
Boukouvalas J and McCann L C
Tetrahedron Letters, 52(11), 1202-1204 (2011)
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)
Michal Plž et al.
Molecules (Basel, Switzerland), 25(18) (2020-09-24)
The co-immobilization of ketoreductase (KRED) and glucose dehydrogenase (GDH) on highly cross-linked agarose (sepharose) was studied. Immobilization of these two enzymes was performed via affinity interaction between His-tagged enzymes (six histidine residues on the N-terminus of the protein) and agarose
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)
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