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

Chemical Properties

Acetoacetic acid, also known as 3-oxobutanoic acid, is a colourless, oily liquid or crystalline substance. It is strongly acidic and unstable. When heated to 100°C, it decomposes vigorously into acetone and carbon dioxide. It is miscible with water and alcohols and has a melting point of 36–37°C. Acetoacetic acid is a ketone body found in abnormal quantities in the blood and urine under certain conditions, such as diabetes.

Uses

In organic syntheses.

Definition

ChEBI: Acetoacetic acid is a 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent. It has a role as a metabolite. It is a ketone body and a 3-oxo fatty acid. It is functionally related to a butyric acid. It is a conjugate acid of an acetoacetate. It is a tautomer of a 3-hydroxy-3-butenoic acid.

Reactivity Profile

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

Health effects

Acetoacetic acid and β-hydroxybutyric acid are both acidic substances that can lead to metabolic acidosis, which may cause damage to the cardiovascular and cerebrovascular systems, impair oxygen utilization, and result in respiratory paralysis. In severe cases, complications such as cerebral edema, respiratory failure, and heart failure may occur, potentially leading to death.

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
• 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 2-cyclopentanonecarboxylate
• METHYL 4-FLUOROBENZOYLACETATE
• Mordant Blue 29
• ALPHA-ACETYL-ALPHA-METHYL-GAMMA-BUTYROLACTONE
• 8-ACETYL DIMETHOXYCOUMARIN
• Oxaloacetic acid