2,3-dihydro-1-benzofuran-3-one

• ChemBase ID: 69604
• Molecular Formular: C8H6O2
• Molecular Mass: 134.13204
• Monoisotopic Mass: 134.03677943
• SMILES: O1CC(=O)c2c1cccc2
• Canonical SMILES: O=C1COc2c1cccc2
• InChI: InChI=1S/C8H6O2/c9-7-5-10-8-4-2-1-3-6(7)8/h1-4H,5H2
• InChIKey: MGKPCLNUSDGXGT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydro-1-benzofuran-3-one
• IUPAC Traditional name: 3(2H)-benzofuranone
• Synonyms: Benzofuran-3(2H)-one; 2H-Benzofuran-3-one; 2,3-Dihydrobenzofuran-3-one; 3-Coumaranone; 1-Benzofuran-3(2H)-one; Coumaran-3-one; Benzo[b]furan-3(2H)-one; 3-Coumaranone; Benzofuran-3(2H)-one; 2,3-dihydro-1-benzofuran-3-one; 3-COUMARANONE; 1-Benzofuran-3(2H)-one; 香豆冉酮; 3-氯杀鼠灵酮; 3-苯并呋喃酮

Database IDs

• CAS Number: 7169-34-8
• EC Number: 000-000-0
• MDL Number: MFCD00051810
• Beilstein Number: 115296
• PubChem SID: 162035330; 24847642
• PubChem CID: 23556

CALCULATED PROPERTIES

• Acid pKa: 8.16738
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0736192
• LogD (pH = 7.4): 1.0061505
• Log P: 1.0745511
• Molar Refractivity: 36.3649 cm^3
• Polarizability: 14.010339 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 101-103 °C; 96 - 98°C; 97-102°C; 97-103°C
• Hydrophobicity(logP): 1.358

Safety Information

• Storage Warning: IRRITANT; Irritant/Light Sensitive/Store under Argon/Keep Cold; Light Sensitive
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 95%; 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C8H6O2

DETAILS

Sigma Aldrich - 12502

Packaging
1, 5 g in glass bottle

REFERENCES

• 3-Coumaranone and its substituted analogues undergo Horner-Wadsworth-Emmons reaction with Diethyl cyanomethylphosphonate, A10218, in the presence of NaH, to give 3-(cyanomethyl)benzofurans, intermediates in a synthesis of antihyperglycemic agents: J. Med. Chem., 35, 1176 (1992).
• Condenses with aromatic aldehydes in the presence of alumina under mild conditions to give aurones, an important class of natural pigments: Tetrahedron Lett., 33, 5937 (1992):