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2(5H)-Furanone

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2(5H)-Furanone Basic information

Product Name:
2(5H)-Furanone
Synonyms:
  • .alpha.,.beta.-Crotonolactone
  • γ-Crotonolactone, 2-Buten-1,4-olide
  • 2,5-Dihydrofuranone
  • 5-Oxo-2,5-dihydrofuran-3-yl ester
  • a,b-Crotonolactone
  • Crotonic acid, 4-hydroxy-
  • 2,5-Dihydrofuran-2-one
  • 2(5H)-Furanone,γ-Crotonolactone, 2-Buten-1,4-olide
CAS:
497-23-4
MF:
C4H4O2
MW:
84.07
EINECS:
207-839-3
Product Categories:
  • Antibiotic
  • Heterocycles
  • Building Blocks
  • C4 to C7
  • Chemical Synthesis
  • Furans
  • Heterocyclic Building Blocks
Mol File:
497-23-4.mol
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2(5H)-Furanone Chemical Properties

Melting point:
4-5 °C(lit.)
Boiling point:
86-87 °C12 mm Hg(lit.)
Density 
1.185 g/mL at 25 °C(lit.)
FEMA 
4138 | 4-HYDROXY-2-BUTENOIC ACID GAMMA-LACTONE
refractive index 
n20/D 1.469(lit.)
Flash point:
214 °F
storage temp. 
2-8°C
form 
Liquid
color 
Clear colorless to pale yellow or amber
Water Solubility 
Immiscible with water.
JECFA Number
2000
BRN 
383585
InChIKey
VIHAEDVKXSOUAT-UHFFFAOYSA-N
CAS DataBase Reference
497-23-4(CAS DataBase Reference)
NIST Chemistry Reference
2(5H)-Furanone(497-23-4)
EPA Substance Registry System
2(5H)-Furanone (497-23-4)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
RTECS 
LU3453000
8-10
Hazard Note 
Irritant
HS Code 
29322980

MSDS

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2(5H)-Furanone Usage And Synthesis

Chemical Properties

2(5H)-Furanone is light brown liquid

Chemical Properties

Colorless to pale brown-yellow clear liquid

Occurrence

Reported found in coffee

Uses

2(5H)-Furanone is a heterocyclic organic compound that is used widely in the synthetic preparation of pharmaceutical goods.

Uses

2(5H)-Furanone is 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

Definition

2(5H)-Furanone is a mycotoxin that contains an α,β-unsaturated lactone moiety.

Hazard

Extremely toxic.

Purification Methods

Fractionally distil the lactone under reduced pressure. IR: (CCl4) 1784 and 1742 cm-1, UV no max above 205nm ( 1160 cm-1 M-1) and 1HR: (CCl3) : 2.15 (pair of triplets 1H), 3.85 (pair of triplets 1H) and 5.03 (triplet 2H). [Price & Judge Org Synth Coll Vol V 255 1973, Smith & Jones Can J Chem 37 2007, 2092 1959, Beilstein 17/9 V 112.]

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