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E35400

Ethyl 2-methylacetoacetate

90%

Synonym(s):

Ethyl 2-methyl-3-oxobutanoate

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$54.70

100 G

$157.00

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About This Item

Linear Formula:
CH3COCH(CH3)CO2C2H5
CAS Number:
609-14-3
Molecular Weight:
144.17
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24894520
EC Number:
210-179-9
Beilstein/REAXYS Number:
1071742
MDL number:
MFCD00009164
Assay:
90%
Form:
liquid

Key Documents

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Quality Level

200

InChI key

FNENWZWNOPCZGK-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

90%

form

liquid

refractive index

n20/D 1.418 (lit.)

bp

187 °C (lit.)

density

1.019 g/mL at 25 °C (lit.)

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This Item
E33203180769690295
Ethyl 2-methylacetoacetate 90%

Sigma-Aldrich

E35400

Ethyl 2-methylacetoacetate

Ethyl isobutyrylacetate 95%

Sigma-Aldrich

E33203

Ethyl isobutyrylacetate

Ethyl 4-chloroacetoacetate 95%

Sigma-Aldrich

180769

Ethyl 4-chloroacetoacetate

Ethyl 4-chloroacetoacetate Arxada quality, ≥97.0% (GC)

Sigma-Aldrich

690295

Ethyl 4-chloroacetoacetate

assay

90%

assay

95%

assay

95%

assay

≥97.0% (GC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

form

liquid

form

liquid

form

liquid

form

liquid

density

1.019 g/mL at 25 °C (lit.)

density

0.98 g/mL at 25 °C (lit.)

density

1.218 g/mL at 25 °C (lit.)

density

1.218 g/mL at 25 °C (lit.)

refractive index

n20/D 1.418 (lit.)

refractive index

n20/D 1.425 (lit.)

refractive index

n20/D 1.452 (lit.)

refractive index

n20/D 1.452 (lit.)

bp

187 °C (lit.)

bp

173 °C (lit.)

bp

115 °C/14 mmHg (lit.)

bp

115 °C/14 mmHg (lit.)

Application

  • Ethyl 2-methylacetoacetate is used as a substrate in the rhenium-catalyzed synthesis of multisubstituted aromatic compounds.[1]
  • It can be employed in the synthesis of coumarin derivatives via Pechmann condensation.[2]
  • It undergoes dehydration to yield conjugated alkynyl and allenyl esters.[1]
  • It is also used in the total synthesis of chlorotonil A,[3] yangjinhualine A,[4] (+)- and (−)-saudin.[5]

Storage Class

10 - Combustible liquids

wgk

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB1807
STBL0993
STBJ7467
STBH5996
STBG3016V

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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)
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)
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
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