537365
Methyl acetoacetate
ReagentPlus®, ≥98.5% (GC)
Synonym(s):
MAA, 3-Oxobutanoic acid methyl ester, Acetoacetic acid methyl ester
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All Photos(3)
About This Item
Linear Formula:
CH3COCH2COOCH3
CAS Number:
Molecular Weight:
116.12
Beilstein:
506727
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
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Synergism between microwave and enzyme catalysis in intensification of reactions and selectivities: transesterification of methyl acetoacetate with alcohols.
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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)
Zinc mediated transesterification of ?-ketoesters and coumarin synthesis.
Chavan SP, et al.
Tetrahedron Letters, 43(47), 8583-8586 (2002)
S Aramaki et al.
Journal of inherited metabolic disease, 14(1), 63-74 (1991-01-01)
The concentrations of 2-methylacetoacetate, 2-methyl-3-hydroxybutyrate and tiglylglycine were determined by gas chromatography-mass spectrometry in urine collected before and for 8 h after loading with 100 mg of isoleucine per kg of body weight. The sum of 2-methylacetoacetate and 2-butanone, a
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