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283754

Sigma-Aldrich

2(5H)-Furanone

98%

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Synonym(s):
γ-Crotonolactone, 2-Buten-1,4-olide
Empirical Formula (Hill Notation):
C4H4O2
CAS Number:
Molecular Weight:
84.07
Beilstein:
383585
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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

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This Item
360872479179468037
2(5H)-Furanone 98%

Sigma-Aldrich

283754

2(5H)-Furanone

form

liquid

form

-

form

-

form

-

refractive index

n20/D 1.469 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.443 (lit.)

bp

86-87 °C/12 mmHg (lit.)

bp

105 °C/0.5 mmHg (lit.)

bp

-

bp

120-121 °C/18 mmHg (lit.)

mp

4-5 °C (lit.)

mp

62-64 °C (lit.)

mp

156-159 °C (lit.)

mp

-

density

1.185 g/mL at 25 °C (lit.)

density

-

density

-

density

1.08 g/mL at 25 °C (lit.)

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

Bottomless glass bottle. Contents are inside inserted fused cone.

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

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