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497-23-4 - 2(5H)-Furanone, 96% - 2-Buten-1,4-olide - gamma-Crotonolactone - L13142 - Alfa Aesar

L13142 2(5H)-Furanone, 96%

CAS Number
497-23-4
Synonyms
2-Buten-1,4-olide
gamma-Crotonolactone

Size Price ($) Quantity Availability
1g 53.90
5g 193.00
25g 740.00
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2(5H)-Furanone, 96%

MDL
MFCD00005376
EINECS
207-839-3

Chemical Properties

Formula
C4H4O2
Formula Weight
84.07
Melting point
3-4°
Boiling Point
212-214°
Flash Point
101°(213°F)
Density
1.197
Refractive Index
1.4690
Solubility
Immiscible with water.

Applications

2(5H)-Furanone is employed in the preparation of 5-substituted 2(5H) furanones (gamma-butenolides) catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts through direct aldol reaction with aromatic aldehydes. Further, it is used in the synthesis of lignans by Michael addition reactions. In addition to this, it is used in three-component Michael-Aldol reactions with an aldehyde and thiolate or carbanion.

Notes

Light and moisture sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Literature References

Reaction with lithiated o-methylbenzophenone derivatives gives fused tricyclic products which are readily converted to arylnaphthofuranone lignans: J. Chem. Soc., Perkin 1, 3013 (1995):

Lejeune, G.; Font, J.; Parella, T.; Alibés, R.; Figueredo, M. Intramolecular Photoreactions of (5S)-5-Oxymethyl-2(5H)-furanones as a Tool for the Stereoselective Generation of Diverse Polycyclic Scaffolds. J. Org. Chem. 2015, 80 (19), 9437-9445.

Sanna, A.; Vispute, T. P.; Huber, G. W. Hydrodeoxygenation of the aqueous fraction of bio-oil with Ru/C and Pt/C catalysts. Appl. Catal., B 2015, 165, 446-456.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P280a-P264-P305+P351+P338-P321-P332+P313-P337+P313

Wear protective gloves and eye/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists:

Other References

Beilstein
383585
Harmonized Tariff Code
2932.20
TSCA
No
RTECS
LU3453000

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