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283754 Sigma-Aldrich

2(5H)-Furanone

98%

Synonym: γ-Crotonolactone, 2-Buten-1,4-olide

  • CAS Number 497-23-4

  • Empirical Formula (Hill Notation) C4H4O2

  • Molecular Weight 84.07

  •  Beilstein/REAXYS Number 383585

  •  EC Number 207-839-3

  •  MDL number MFCD00005376

  •  PubChem Substance ID 24857130

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C4 to C7, Chemical Synthesis, Furans, Heterocyclic Building Blocks More...
assay   98%
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.)
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. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains.

Application

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

Packaging

1, 5 g in glass bottle

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
LU3453000
Flash Point(F) 
213.8 °F - closed cup
Flash Point(C) 
101 °C - closed cup

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Protocols & Articles
Peer-Reviewed Papers
15

References

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