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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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Zinc mediated transesterification of ?-ketoesters and coumarin synthesis.
Chavan SP, et al.
Tetrahedron Letters, 43(47), 8583-8586 (2002)
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)
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)
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)
Xiao Hu et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(47), 16796-16801 (2014-11-05)
Much remains unknown regarding speciation. Host-pathogen interactions are a major driving force for diversification, but the genomic basis for speciation and host shifting remains unclear. The fungal genus Metarhizium contains species ranging from specialists with very narrow host ranges to
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