2-oxo-2H-pyran-5-carboxylic acid

• ChemBase ID: 80424
• Molecular Formular: C6H4O4
• Molecular Mass: 140.09356
• Monoisotopic Mass: 140.01095861
• SMILES: o1cc(C(=O)O)ccc1=O
• Canonical SMILES: O=c1ccc(co1)C(=O)O
• InChI: InChI=1S/C6H4O4/c7-5-2-1-4(3-10-5)6(8)9/h1-3H,(H,8,9)
• InChIKey: ORGPJDKNYMVLFL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxo-2H-pyran-5-carboxylic acid
• IUPAC Traditional name: 6-oxopyran-3-carboxylic acid
• Synonyms: Coumalic acid; 5-Carboxy-2-pyrone; 2-Oxo-2H-pyran-5-carboxylic acid; 2-Pyrone-5-carboxylic acid; 2-Oxo-2H-pyran-5-carboxylic acid; Coumalic acid; CouMalic acid; 2-吡喃酮-5-羧酸; 2-氧代-2H-吡喃-5-羧酸; 香豆酸

Database IDs

• CAS Number: 500-05-0
• EC Number: 207-899-0
• MDL Number: MFCD00006644
• Beilstein Number: 119747
• Merck Index: 142557
• PubChem SID: 24893071; 162067544; 24856855
• PubChem CID: 68141

CALCULATED PROPERTIES

• Acid pKa: 2.9427583
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.333375
• LogD (pH = 7.4): -3.2999282
• Log P: 0.18107638
• Molar Refractivity: 32.0947 cm^3
• Polarizability: 11.998467 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 203-205 °C (dec.)(lit.); 203-205(dec.)°C; ca 208°C dec.
• Boiling Point: 218 °C/120 mmHg(lit.); 218°C/120mm; 218°C/120mm

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (T); 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C6H4O4
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - C85409

General description
Decarboxylates to α-pyrone, a Diels-Alder diene.
Packaging
25 g in poly bottle
5 g in glass bottle

REFERENCES

• Precursor, by decarboxylation, of 2-pyrone (ɑ-pyrone), a valuable diene in the Diels-Alder reaction: Org. Synth. Coll.,5, 982 (1973).