1H,3H,4H,5H,6H-cyclopenta[c]furan-1,3-dione

• ChemBase ID: 145511
• Molecular Formular: C7H6O3
• Molecular Mass: 138.12074
• Monoisotopic Mass: 138.03169405
• SMILES: C1CC2=C(C1)C(=O)OC2=O
• Canonical SMILES: O=C1OC(=O)C2=C1CCC2
• InChI: InChI=1S/C7H6O3/c8-6-4-2-1-3-5(4)7(9)10-6/h1-3H2
• InChIKey: GBBPFLCLIBNHQO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H,3H,4H,5H,6H-cyclopenta[c]furan-1,3-dione
• IUPAC Traditional name: 4H,5H,6H-cyclopenta[c]furan-1,3-dione
• Synonyms: 1-Cyclopentene-1,2-dicarboxylic anhydride; 1-环戊烯-1,2-二羧酸酐

Database IDs

• CAS Number: 3205-94-5
• MDL Number: MFCD00013330
• Beilstein Number: 123650
• PubChem SID: 162239716; 24859125
• PubChem CID: 324854

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.331868
• LogD (pH = 7.4): 1.331868
• Log P: 1.331868
• Molar Refractivity: 32.9146 cm^3
• Polarizability: 12.835556 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 42-45 °C; 42-45 °C(lit.)
• Boiling Point: 133-135 °C/10 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Refractive Index: n20/D 1.4978(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥94% (T); 96%
• Grade: technical
• Empirical Formula (Hill Notation): C7H6O3

DETAILS

Sigma Aldrich - 318353

Application
Valuable Diels-Alder dienophile, for example, in approach to the bicycloundecane system in taxanes.1,2
Packaging
1 g in glass bottle

Sigma Aldrich - 29822

Other Notes
Preparation of polycyclic compounds via Diels-Alder CA1,2