Methyl acetoacetate

Methyl acetoacetate
Names
	IUPAC name methyl 3-oxobutanoate
	Other names Acetoacetic acid methyl ester; Methyl acetylacetate; 3-Oxobutanoic acid methyl ester;
Identifiers
CAS Number	105-45-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:166454;
ChEMBL	ChEMBL3186053;
ChemSpider	13874867 ;
ECHA InfoCard	100.003.000
EC Number	203-299-8;
PubChem CID	7757;
UNII	CW4I82QAX1;
UN number	1993
CompTox Dashboard (EPA)	DTXSID9026716 ;
	InChI InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3 Key: WRQNANDWMGAFTP-UHFFFAOYSA-N ;
	SMILES COC(=O)CC(C)=O;
Properties
Chemical formula	C5H8O3
Molar mass	116.116 g·mol−1
Appearance	Colourless liquid
Odor	Fruit or rum
Density	1.076 g/cm3
Boiling point	166 °C (331 °F; 439 K)
Solubility in water	40 g/100 mL (20 °C)
Refractive index (nD)	1.411
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P305+P351+P338
NFPA 704 (fire diamond)	2 2
Flash point	70 °C (158 °F; 343 K)
Related compounds
Related esters	Ethyl acetoacetate; Ethyl acetate; Diethyl malonate;
Related compounds	Acetone; Acetylacetone; Diketene;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The organic compound methyl acetoacetate is the methyl ester of acetoacetic acid. It is a colorless liquid. It is used as a chemical intermediate. Many of its properties are similar to those for ethyl acetoacetate, which is more common.

At large scale, methyl acetoacetate is industrially produced by treatment of diketene with methanol.^[2]

Safety and environmental considerations

Methyl acetoacetate has low toxicity to animals. It is highly biodegradable.^[2]

^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2021-12-19.
^ ^a ^b Riemenschneider, Wilhelm; Bolt, Hermann M. (2005). "Esters, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_565.pub2. ISBN 3527306730.