283754

2(5H)-Furanone

98%

• Synonym(s): γ-Crotonolactone, 2-Buten-1,4-olide
• Empirical Formula (Hill Notation): C₄H₄O₂
• CAS Number: 497-23-4
• Molecular Weight: 84.07
• Beilstein: 383585
• EC Number: 207-839-3
• MDL number: MFCD00005376
• UNSPSC Code: 12352100
• PubChem Substance ID: 24857130
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: 98%
• form: liquid
• refractive index: n20/D 1.469 (lit.)
• bp: 86-87 °C/12 mmHg (lit.)
• mp: 4-5 °C (lit.)
• density: 1.185 g/mL at 25 °C (lit.)
• functional group: ester
• storage temp.: 2-8°C
• SMILES string: O=C1OCC=C1
• InChI: 1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
• InChI key: VIHAEDVKXSOUAT-UHFFFAOYSA-N

Description

General description

Chiral urea compounds catalyzed hetero-Michael addition reaction of 2(5H)-furanone (γ-crotonolactone) to pyrrolidine[1]. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains[2].

Application

2(5H)-Furanone (γ-Crotonolactone) has been used in:

• synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid[3]
• synthesis of 5-substituted 2(5H) furanones (γ-butenolides) via direct aldol reaction with aromatic aldehydes catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts[4]
• Michael addition reactions[5] for synthesis of lignans[6]
• three-component Michael-Aldol reactions with an aldehyde anda thiolate[7] or carbanion[8]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 213.8 °F - closed cup
• Flash Point(C): 101 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves