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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:166454
ChEMBL
  • ChEMBL3186053
ChemSpider
  • 13874867 checkY
ECHA InfoCard 100.003.000 Edit this at Wikidata
EC Number
  • 203-299-8
PubChem CID
  • 7757
UNII
  • CW4I82QAX1
UN number 1993
CompTox Dashboard (EPA)
  • DTXSID9026716 Edit this at Wikidata
InChI
  • InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3 checkY
    Key: WRQNANDWMGAFTP-UHFFFAOYSA-N checkY
  • 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)
1.411
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H319
P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
2
2
Flash point 70 °C (158 °F; 343 K)
Related compounds
Related esters
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

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]

References

  1. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2021-12-19.
  2. ^ 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.
  • International Chemical Safety Card 1024
  • Inchem properties database