1,3-Acetonedicarboxylic acid

Chemical properties

white to off-white powder

Physical properties

Acetonedicarboxylic acid forms colorless crystals that are readily soluble in water and ethanol, and sparingly soluble in trichloromethane and diethyl ether. It melts with decomposition at 138 ℃.

The Uses of 1,3-Acetonedicarboxylic acid

1,3-Acetonedicarboxylic acid has been applied as a stimuli for reversible time-controlled pH modulation. It is cheaper and safer than commonly used reagents and enables the switch of the pH of a chemical system through its catalyzed decarboxylation. This was notably applied in the reversible disruption of a hydrogel. It is used as a building block in organic chemistry. It is also used in synthesising hetrocyclic rings and in the Weiss-Cook reaction, which involves the preparation of cis-bicyclo[3.3.0]octane-3,7-dione by reacting with diacyl (1,2 ketone). Its presence in human urine is used as a diagnostic test for the overgrowth of harmful gut flora, such as Candida albicans. 1,3-Acetonedicarboxylic acid is used in the synthesis of benzodiazepine derivatives. Also used in the synthesis of orally available hepatitis C virus polymerase inhibitors.

Definition

ChEBI: 3-Oxoglutaric acid is an oxo carboxylic acid.

Production Methods

1,3-Acetonedicarboxylic acid is produced from citric acid [77-92-9] by many industrial processes that differ only slightly. Citric acid is treated with oleum and reacts to yield acetonedicarboxylic acid via decarbonylation and dehydration.
Other possible production methods include reaction of acetone with carbon dioxide, oxidation of citric acid with chlorosulfuric acid, or reaction of ketene with phosgene.

Flammability and Explosibility

Non flammable

Description

1,3-Acetonedicarboxylic acid is an intriguing molecule possessing two pendant carboxylic acid functions that can potentially be involved in double biomimetic-like decarboxylative enolate formation, rendering the corresponding acetone α,α′-dianion readily available. Prepared on a large scale from raw material, namely citric acid, it can act as a potentially reactive di-nucleophilic acetone surrogate. Robinson famously applied this property in his 1917 tropinone synthesis and has since then found intensive utilization in the synthesis of tropinone-like skeletons.

Purification Methods

Crystallise it from ethyl acetate and store it over P2O5. It decarboxylates in hot water. [Beilstein 3 IV 1816.]