3-oxopentanedioic acid

• ChemBase ID: 70093
• Molecular Formular: C5H6O5
• Molecular Mass: 146.09814
• Monoisotopic Mass: 146.02152329
• SMILES: C(C(=O)CC(=O)O)C(=O)O
• Canonical SMILES: O=C(CC(=O)O)CC(=O)O
• InChI: InChI=1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)
• InChIKey: OXTNCQMOKLOUAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxopentanedioic acid
• IUPAC Traditional name: acetonedicarboxylic acid
• Synonyms: 1,3-Acetonedicarboxylic acid; 3-oxopentanedioic acid; 3-ketoglutaric acid; β-ketoglutaric acid; Acetonedicarboxylic acid; 3-Oxopentane-1,5-dioic acid; Acetone-1,3-dicarboxylic acid; 1,3-Acetonedicarboxylic acid; 1,3-Acetonedicarboxylic acid; 3-Oxoglutaric acid; β-KETOGLUTARIC ACID; Acetone-1,3-dicarboxylic acid; 3-氧代戊二酸; 1,3-丙酮二羧酸; 丙酮1,3-二羧酸

Database IDs

• CAS Number: 542-05-2
• EC Number: 208-797-9
• MDL Number: MFCD00002711
• Beilstein Number: 1447081
• Merck Index: 1468
• PubChem SID: 24844888; 162035818; 24850123
• PubChem CID: 68328
• Chemspider ID: 61623
• Wikipedia Title: Acetonedicarboxylic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.2495573
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.8336027
• LogD (pH = 7.4): -6.730684
• Log P: -0.1092633
• Molar Refractivity: 28.883 cm^3
• Polarizability: 11.379348 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 133 - 135°C; 133 °C (dec.); 133 °C (dec.)(lit.); ca 132°C dec.
• Boiling Point: 408,4 °C (760mm Hg)
• Flash Point: 214,9 °C
• Density: 1,499 g/cm^3
• Hydrophobicity(logP): -0.598

Safety Information

• Storage Condition: 0°C
• Storage Warning: Hygroscopic; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95.0% (T); 95%; 95+%; 97%; 98%
• Grade: purum; technical grade
• Ignition Residue: ≤0.3%
• Impurities: ≤0.5% H2SO4
• Linear Formula: HOOCCH2COCH2COOH

DETAILS

Sigma Aldrich - 165115

Packaging
25, 100 g in glass bottle

REFERENCES

• For a more recent analogous example of the synthesis of azabicyclo[3.3.1]nonan-3-one derivatives, see: J. Med. Chem., 36, 3707 (1993).
• For use in Robinson's classical one-step synthesis of pseudopelletierine, see: Org. Synth. Coll., 4, 816 (1963):