Acetoacetic Acid Chemical Properties

Melting point:

36-37°

Boiling point:

131.37°C (rough estimate)

Density 

1.1717 (rough estimate)

refractive index 

1.4540 (estimate)

pka

3.58(at 18℃)

PH

3.4(1 mM solution);2.83(10 mM solution);2.3(100 mM solution)

Water Solubility 

sol H2O, alcohol

LogP

-0.467 (est)

Safety Information

RIDADR 

1759

HazardClass 

8

PackingGroup 

III

Acetoacetic Acid Usage And Synthesis

Uses

In organic syntheses.

Definition

ChEBI: A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.

Reactivity Profile

Acetone enolate equivalent in alkylations, carbonyl additions, conjugate additions, and diazonium ion coupling reactions[4-7].

Synthesis

Traditionally prepared by base hydrolysis of Ethyl Acetoacetate. A high yield synthesis by acid hydrolysis of Diketene is also reported[1-3].

storage

Handling, Storage, and Precautions: acetoacetic acid is extremely hygroscopic but can be stored under vacuum in a freezer for several weeks with little change. It decomposes rapidly to acetone and carbon dioxide when heated above the melting point. Use in a fume hood.

References

1. Grayson, D. H.; Tuite, M. R. J. JCS(P1) 1986, 2137
2. Grande, K. D.; Rosenfeld, S. M. JOC 1980, 45, 1626.
3. Krueger, R. C. JACS 1952, 74, 5536.
4. Kjonaas, R. A.; Patel, D. D. TL 1984, 25, 5467.
5. Grayson, D. H.; Tuite, M. R. J. JCS(P1) 1986, 2137.
6. Fujii, M.; Terao, Y.; Sekiya, M. CPB 1974, 22, 2675.
7. (a) Parmerter, S. M. OR 1959, 10, 1. (b) Phillips, R. R. OR 1959, 10, 143.

Acetoacetic Acid(541-50-4)Related Product Information

• 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester
• Ethyl 4-chloroacetoacetate
• Oxobutanedioic acid
• NAPHTHOCHROME GREEN
• 1,3-Acetonedicarboxylic acid
• 3-(2-FLUORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
• 2-Acetylbutyrolactone
• Ethyl 4,4,4-trifluoroacetoacetate
• Nalidixic acid
• Methyl 4-chloro-3-oxo-butanoate
• Diethyl succinosuccinate
• Ethyl 2-oxocyclohexanecarboxylate
• Ethyl 2-oxocyclopentanecarboxylate
• METHYL 4-FLUOROBENZOYLACETATE
• Mordant Blue 29
• ALPHA-ACETYL-ALPHA-METHYL-GAMMA-BUTYROLACTONE
• 8-ACETYL DIMETHOXYCOUMARIN
• Methyl 2-cyclopentanonecarboxylate