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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 |  |
| | 2(5H)-Furanone Chemical Properties |
| Melting point | 4-5 °C (lit.) | | Boiling point | 86-87 °C/12 mmHg (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.) | | Fp | 214 °F | | storage temp. | 2-8°C | | solubility | Chloroform, Ethyl Acetate (Slightly) | | form | Liquid | | color | Clear colorless to pale yellow or amber | | Odor | buttery | | Odor Type | buttery | | Water Solubility | Immiscible with water. | | JECFA Number | 2000 | | BRN | 383585 | | Stability: | Moisture Sensitive | | InChIKey | VIHAEDVKXSOUAT-UHFFFAOYSA-N | | LogP | -0.600 | | 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) |
| | 2(5H)-Furanone Usage And Synthesis |
| Chemical Properties | Colorless to pale brown-yellow clear liquid
| | Chemical Properties | 2(5H)-Furanone is light brown liquid
| | Occurrence | Reported found in coffee | | Uses | 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. | | 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.
| | 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. | | 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.] |
| | 2(5H)-Furanone Preparation Products And Raw materials |
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