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537365

Sigma-Aldrich

Methyl acetoacetate

ReagentPlus®, ≥98.5% (GC)

Synonym(s):

MAA, 3-Oxobutanoic acid methyl ester, Acetoacetic acid methyl ester

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About This Item

Linear Formula:
CH3COCH2COOCH3
CAS Number:
105-45-3
Molecular Weight:
116.12
Beilstein:
506727
EC Number:
203-299-8
MDL number:
MFCD00008784
UNSPSC Code:
12352100
PubChem Substance ID:
24878214
NACRES:
NA.22

product line

ReagentPlus®

Assay

≥98.5% (GC)

autoignition temp.

536 °F

manufacturer/tradename

Sigma-Aldrich

refractive index

n20/D 1.419 (lit.)

bp

169-170 °C/70 mmHg (lit.)

mp

−80 °C (lit.)

density

1.076 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CC(C)=O

InChI

1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3

InChI key

WRQNANDWMGAFTP-UHFFFAOYSA-N

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Application

Methyl acetoacetate (MAA) can be used as a reactant for:
  • Transesterification with alcohols by using various catalysts.
  • The synthesis of 4-methylcoumarins with phenol in presence of zinc and I2 as catalysts.
  • Asymmetric heterogeneous hydrogenation reactions by transition metal catalysts.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

158.0 °F - closed cup

Flash Point(C)

70 °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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Enantioselective hydrogenation of methyl acetoacetate catalyzed by nickel supported on activated carbon or graphite.
Wolfson A, et al.
Applied Catalysis A: General, 208(1-2), 91-98 (2001)
Synergism between microwave and enzyme catalysis in intensification of reactions and selectivities: transesterification of methyl acetoacetate with alcohols.
Yadav GD and Lathi PS
J. Mol. Catal. A: Chem., 223(1-2), 51-56 (2004)
Zinc mediated transesterification of ?-ketoesters and coumarin synthesis.
Chavan SP, et al.
Tetrahedron Letters, 43(47), 8583-8586 (2002)
Synthesis and studies of 6, 6′ -BINAP derivatives for the heterogeneous asymmetric hydrogenation of methyl acetoacetate.
Saluzzo C, et al.
Tetrahedron Asymmetry, 13(11), 1141-1146 (2002)
Karl Sörelius et al.
Circulation, 130(24), 2136-2142 (2014-11-08)
Mycotic aortic aneurysm (MAA) is a rare and life-threatening disease. The aim of this European multicenter collaboration was to study the durability of endovascular aortic repair (EVAR) of MAA, by assessing late infection-related complications and long-term survival. All EVAR treated
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