2-OXO-1,3-PROPANE DICARBOXYLIC ACID

2-OXO-1,3-PROPANE DICARBOXYLIC ACID - Names and Identifiers

Name	1,3-Acetonedicarboxylic acid
Synonyms	3-oxopentanedioate 3-Oxoglutaric acid 3-Ketoglutaric acid 3-oxo-pentanedioicaci 3-Oxopentanedioic acid 1,3-Acetonediacrboxylicacid 3-Oxopentane-1,5-dioic acid 1,3-Acetonedicarboxylic acid Acetone-1,3-dicarboxylic acid 1,3-Acetone diacrboxylic acid 1,3-ACETONEDICARBOXYLIC ACID, TECH. 2-OXO-1,3-PROPANE DICARBOXYLIC ACID 1,3-ACETONEDICARBOXYLIC ACID, 3-KETOGLUTARIC ACID
CAS	542-05-2
EINECS	208-797-9
InChI	InChI=1/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)/p-2
InChIKey	OXTNCQMOKLOUAM-UHFFFAOYSA-N

2-OXO-1,3-PROPANE DICARBOXYLIC ACID - Physico-chemical Properties

Molecular Formula	C5H6O5
Molar Mass	146.1
Density	1.2821 (rough estimate)
Melting Point	133 °C (dec.) (lit.)
Boling Point	185.67°C (rough estimate)
Flash Point	214.9°C
Water Solubility	soluble
Solubility	DMSO (Slightly, Heated), Methanol (Slightly)
Vapor Presure	0.005Pa at 25℃
Appearance	Crystalline Powder
Color	White
Merck	14,68
BRN	1447081
pKa	pK (25°) 3.10
Storage Condition	-20°C
Stability	Unstable in Solution
Sensitive	Hygroscopic
Refractive Index	1.3920 (estimate)
Physical and Chemical Properties	colorless needle-like crystals. melting point 135 °c (decomposition). soluble in water and alcohol, insoluble in chloroform and benzene, slightly soluble in ether and ethyl acetate. Storage conditions: 2-8°C
Use	Pharmaceutical intermediates for atropine, anisodamine and other anticholinergic drugs.

2-OXO-1,3-PROPANE DICARBOXYLIC ACID - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	R44 - Risk of explosion if heated under confinement R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing.
WGK Germany	3
FLUKA BRAND F CODES	3
TSCA	Yes
HS Code	29183000

2-OXO-1,3-PROPANE DICARBOXYLIC ACID - Reference Information

LogP	-0.5 at 30℃
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
introduction	1, 3-acetone dicarboxylic acid is colorless needle-like crystal. Melting point 135 ℃ (decomposition). Easily soluble in water and alcohol, insoluble in chloroform and benzene, slightly soluble in ether and ethyl acetate. 1, 3-acetone dicarboxylic acid is an aliphatic chain molecule and plays an important role in the field of biomedicine. 1, 3-acetone dicarboxylic acid (Dimethylacetone-1,) is a medical intermediate. It was used in the synthesis of atropine and Aromaine in the 20th century. In this century, it has been widely used in the synthesis of antibiotic drugs because it has been found to have certain antibacterial activity.
application	1, 3-acetone dicarboxylic acid is an important intermediate of anti-inflammatory and analgesic sodium zomelate (ZomepiracSodium) and strontium ranelate (StrontiumRanelate). 1, 3-acetone dicarboxylic acid is an important organic synthesis and pharmaceutical intermediates, which can be used to synthesize drugs such as endo-type pendin, graneus, benzoate, strontium ranelate, etc. Therefore, the research on the synthesis methodology of 1,3-acetone dicarboxylic acid has important application prospects.
preparation	50g (0.5mol) of concentrated hydrochloric acid (chemically pure, 36.5%) is added to a 250ml three-mouth flask, under full stirring, the temperature is raised to 30 ℃, 42.9g (0.436mol) of epichlorohydrin is added dropwise, the dropwise addition is completed for about 45min, and the heat preservation reaction is carried out for 2h. After the reaction is completed, the organic phase is separated into 1,3-dichloropropanol, and it is dehydrated with anhydrous sodium carbonate at room temperature. In a 250ml three-mouth flask, 138.8g of 30% sodium cyanide aqueous solution (0.85mol) is added, the temperature is raised to reflux, the organic phase of the step reaction is slowly added dropwise, and the step-by-step reaction is completed dropwise for about 1h, the heat preservation reaction is carried out for 2h, the temperature is cooled to room temperature, the organic phase is separated into 1,3-dinitronitrile propanol, and the organic phase is washed with 30ml * 3 water. In a 250ml three-mouth flask, 1, 3-dinitrile propanol, 111.1g 75% sulfuric acid and 50ml xylene are added, heated at 135-140 ℃ for reflux reaction for 24 hours, then cooled to room temperature and added 50ml of water to precipitate crystals as 3-hydroxyglutaric acid. In a 250ml three-mouth flask, 100ml of aqueous solution containing 38.7g (0.39mol) of chromium trioxide is added, cooled to 20 ℃, then 3-hydroxyglutaric acid collected in the previous reaction is added, stirred fully, 105g of aqueous solution containing 77.4g of concentrated sulfuric acid is slowly added dropwise, and the adding is completed dropwise for about 5h, and the heat preservation reaction is carried out after stirring for 3h. Extraction with ethyl acetate 100ml * 5, desolubilized to obtain a white acicular solid of acetone dicarboxylic acid.
uses	pharmaceutical intermediates for anticholinergic drugs such as atropine and anisodamine.
production method	citric acid is used as raw material and deformic acid is removed in the presence of concentrated sulfuric acid. In the industrial process, fuming sulfuric acid is first put into the reaction tank, and citric acid is added in stages under stirring when it is cooled below 50°C. The weight ratio is citric acid: fuming sulfuric acid 1:2.34. After the feeding is finished, the temperature is raised to 40-45 ℃, and the temperature is kept warm for 3 hours, then the temperature is lowered to below 10 ℃, normal water is added dropwise (the temperature is kept below 40 ℃), then cold to about 15 ℃, centrifuge, rinse with ice water, and spin dry to obtain the finished product.