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Sigma-Aldrich

Methyl acetoacetate

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

Sinonimo/i:

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

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About This Item

Formula condensata:
CH3COCH2COOCH3
Numero CAS:
Peso molecolare:
116.12
Beilstein:
506727
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:

Grado

produced by Wacker Chemie AG, Burghausen, Germany

Saggio

≥99.0% (GC)

Temp. autoaccensione

536 °F

Produttore/marchio commerciale

Wacker Chemie AG

Indice di rifrazione

n20/D 1.419 (lit.)

P. eboll.

169-170 °C/70 mmHg (lit.)

Punto di fusione

−80 °C (lit.)

Solubilità

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

Densità

1.076 g/mL at 25 °C (lit.)

Stringa SMILE

COC(=O)CC(C)=O

InChI

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

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Descrizione generale

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

Applicazioni

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

Altre note

prices for bulk quantities on request

Pittogrammi

Corrosion

Avvertenze

Danger

Indicazioni di pericolo

Consigli di prudenza

Classi di pericolo

Eye Dam. 1

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

158.0 °F - closed cup

Punto d’infiammabilità (°C)

70 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


Certificati d'analisi (COA)

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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
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)
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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