Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

10913

Sigma-Aldrich

Methyl acetoacetate

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

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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:
57646849

grade

produced by Wacker Chemie AG, Burghausen, Germany

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

Looking for similar products? Visit Product Comparison Guide

General description

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.

Application

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.

Other Notes

prices for bulk quantities on request

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service