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10913

Sigma-Aldrich

Methyl acetoacetate

produced by Wacker Chemie AG, Burghausen, Germany, ≥99.0% (GC)

Sinónimos:

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

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About This Item

Fórmula lineal:
CH3COCH2COOCH3
Número de CAS:
105-45-3
Peso molecular:
116.12
Beilstein/REAXYS Number:
506727
EC Number:
203-299-8
MDL number:
MFCD00008784
UNSPSC Code:
12352100
PubChem Substance ID:
57646849
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grade

produced by Wacker Chemie AG, Burghausen, Germany

Quality Level

100

assay

≥99.0% (GC)

autoignition temp.

536 °F

manufacturer/tradename

Wacker Chemie AG

refractive index

n20/D 1.419 (lit.)

bp

169-170 °C/70 mmHg (lit.)

mp

−80 °C (lit.)

solubility

H2O: soluble 2 parts
alcohol: miscible
diethyl ether: miscible

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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General description

Methyl acetoacetate undergoes asymmetric hydrogenation to form (R)-(-)-methyl-3-hydroxybutyrate in the presence of enantioselective Ni/SiO2 catalysts[1]. It undergoes Pechmann reactions with phenols in various ionic liquids[2].

Application

Methyl acetoacetate was used in development of a simple and cost effective method for monitoring of trace formaldehyde in air[3]. It was used to study the substrate specificity of NADPH-dependent diacetyl reductase in Escherichia coli[4].

Other Notes

prices for bulk quantities on request

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

158.0 °F - closed cup

flash_point_c

70 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
S50542V
S50542
S44161
S36666
449875/1

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P Silber et al.
Journal of bacteriology, 118(3), 919-927 (1974-06-01)
A reduced nicotinamide adenine dinucleotide phosphate (NADPH)-dependent reductase with the ability to reduce diacetyl has been isolated from Escherichia coli and has been purified 800-fold to near homogeneity. The product of the reduction of diacetyl was shown to be acetoin.
Pechmann reaction in non-chloroaluminate acidic ionic liquids under solvent-free conditions.
Gu Y, et al.
Advanced Synthesis & Catalysis, 347(4), 512-516 (2005)
The enantioselective hydrogenation of methyl acetoacetate over supported nickel catalysts: I. The modification procedure.
Keane MA and Webb G.
J. Catal., 136(1), 1-15 (1992)
Opas Bunkoed et al.
Analytica chimica acta, 659(1-2), 251-257 (2010-01-28)
We report the development of transparent sol-gels with entrapped sensitive and selective reagents for the detection of formaldehyde. The sampling method is based on the adsorption of formaldehyde from the air and reaction with beta-diketones (for example acetylacetone) in a
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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