1,3-Acetonedicarboxylic acid Chemical Properties

Melting point:

133 °C (dec.) (lit.)

Boiling point:

185.67°C (rough estimate)

Density 

1.2821 (rough estimate)

vapor pressure 

0.005Pa at 25℃

refractive index 

1.3920 (estimate)

storage temp. 

-20°C

solubility 

DMSO (Slightly, Heated), Methanol (Slightly)

pka

pK (25°) 3.10

form 

Crystalline Powder

color 

White

Water Solubility 

soluble

Sensitive 

Hygroscopic

Merck 

14,68

BRN 

1447081

Stability:

Unstable in Solution

InChIKey

OXTNCQMOKLOUAM-UHFFFAOYSA-N

LogP

-0.5 at 30℃

CAS DataBase Reference

542-05-2(CAS DataBase Reference)

EPA Substance Registry System

Pentanedioic acid, 3-oxo- (542-05-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

44-36/37/38

Safety Statements 

22-24/25-37/39-26-36

WGK Germany 

3

F 

3

TSCA 

Yes

HS Code 

29183000

MSDS

• Language:English Provider:3-Oxoglutaric acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,3-Acetonedicarboxylic acid Usage And Synthesis

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 ℃.

Uses

β-Ketoglutaric Acid is used in the synthesis of benzodiazepine derivatives. Also used in the synthesis of orally available hepatitis C virus polymerase inhibitors.

Uses

Acetone-1,3-dicarboxylic acid is used as a building block in organic chemistry. It is also used in the synthesis of 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.

Definition

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

Production Methods

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

Purification Methods

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

1,3-Acetonedicarboxylic acid(542-05-2)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Diacetone Alcohol
• 1,3-Dihydroxyacetone
• Hyaluronic acid
• Citric acid
• Dibenzylideneacetone
• 2,5-PYRIDINEDICARBOXYLIC ACID
• Folic acid
• Diethyl ketomalonate
• 2,2-Dipropylmalonic acid
• Diethyl propylmalonate
• Ascoric Acid
• Phenylacetone
• Propiophenone
• Diethyl-1,3-acetonedicarboxylic acid,1,3-ACETONEDICARBOXYLIC ACID DIETHYL ESTER,ACETONEDICARBOXYLIC ACID DIETHYL ESTER,Acetonedicarboxylic acid diethylether
• 3,3'-CARBONYLBIS(7-DIETHYLAMINOCOUMARIN)
• 3,3'-CARBONYLBIS(7-METHOXYCOUMARIN)
• 1,3-Acetonedicarboxylic acid anhydride,1,3-ACETONEDICARBOXYLIC ACID ANHYDRIDE 98,1,3-Acetonedicarboxylic acid anhydride 98%