2,5-dihydrofuran-2-one

• ChemBase ID: 65086
• Molecular Formular: C4H4O2
• Molecular Mass: 84.07336
• Monoisotopic Mass: 84.02112937
• SMILES: C1C=CC(=O)O1
• Canonical SMILES: C1OC(=O)C=C1
• InChI: InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
• InChIKey: VIHAEDVKXSOUAT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dihydrofuran-2-one
• IUPAC Traditional name: 2(5H)-furanone; 2-(5H)-furanone
• Synonyms: 2,5-dihydrofuran-2-one; gamma-Crotonolactone; 2-Buten-1,4-olide; 2(5H)-Furanone; γ-Crotonolactone; furan-2-one; γ-crotonolactone; β-angelica lactone; butenolide; 2-Furanone; 2(5H)-Furanone; 2-Buten-1,4-olide , gamma-Crotonolactone; Furan-2(5H)-one; γ-巴豆酰内酯; 2(5H)-呋喃酮; 2(5H)-呋喃酮; γ-巴豆酰内酯

Database IDs

• CAS Number: 497-23-4
• EC Number: 207-839-3
• MDL Number: MFCD00005376
• Beilstein Number: 383585
• PubChem SID: 24857130; 24856924; 162030825
• PubChem CID: 10341
• CHEBI ID: 38118
• CHEMBL: 166223
• Chemspider ID: 9917
• KEGG ID: C17601
• MeSH Name: butenolide
• Wikipedia Title: 2-Furanone

CALCULATED PROPERTIES

• Acid pKa: 7.3667917
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.53076017
• LogD (pH = 7.4): 0.21920194
• Log P: 0.5366156
• Molar Refractivity: 21.2474 cm^3
• Polarizability: 7.930509 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 3-4°C; 4 - 5°C (Source); 4-5 °C(lit.)
• Boiling Point: 212-214°C; 86 - 87°C (12 mm Hg, Source); 86-87 °C/12 mmHg(lit.)
• Flash Point: 101 °C; 101°C(213°F); 213.8 °F
• Density: 1.185 g/cm^3, liquid; 1.185 g/mL at 25 °C(lit.); 1.197
• Refractive Index: 1.4690; n20/D 1.469(lit.); n20/D 1.471
• Hydrophobicity(logP): -0.467

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: LU3453000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.5% (GC); 95%; 96%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C4H4O2

DETAILS

Sigma Aldrich - 283754

Packaging
1, 5 g in glass bottle
Application
A versatile reagent used in Michael addition reactions1 for synthesis of lignans.2 Also employed in three-component Michael-Aldol reactions with an aldehyde anda thiolate3 or carbanion.4

Sigma Aldrich - 28005

Other Notes
Review1

REFERENCES

• Reaction with lithiated o-methylbenzophenone derivatives gives fused tricyclic products which are readily converted to arylnaphthofuranone lignans: J. Chem. Soc., Perkin 1, 3013 (1995):