283754
2(5H)-Furanone
98%
Synonym(s):
γ-Crotonolactone, 2-Buten-1,4-olide
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About This Item
Empirical Formula (Hill Notation):
C4H4O2
CAS Number:
Molecular Weight:
84.07
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-839-3
Beilstein/REAXYS Number:
383585
MDL number:
Assay:
98%
Form:
liquid
InChI key
VIHAEDVKXSOUAT-UHFFFAOYSA-N
InChI
1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
SMILES string
O=C1OCC=C1
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
Quality Level
Related Categories
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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
213.8 °F - closed cup
flash_point_c
101 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Tetrahedron, 49, 8073-8073 (1993)
Tetrahedron, 49, 9039-9039 (1993)
Yoshihiro Sohtome et al.
Chemical & pharmaceutical bulletin, 52(4), 477-480 (2004-04-02)
Chiral urea compounds 10a-g were synthesized as catalysts for conjugate addition of pyrrolidine (2) to gamma-crotonolactone (3). In the presence of a catalytic amount of the chiral ureas, this hetero-Michael reaction was greatly accelerated. Asymmetric induction was observed with the
Tetrahedron, 49, 4173-4173 (1993)
Alexey S Vasilchenko et al.
Frontiers in microbiology, 11, 556063-556063 (2020-10-20)
In this work, we report the isolation and detailed functional characterization for the new non-ribosomally synthesized antibiotic 5812-A/C, which was derived from metabolites of Streptomyces roseoflavus INA-Ac-5812. According to its chemical structure, the studied 5812-A/C preliminary is composed of a
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