2(5H)-Furanone

Base Information

• Chemical Name: 2(5H)-Furanone
• CAS No.: 497-23-4
• Molecular Formula: C4H4O2
• Molecular Weight: 84.0746
• Hs Code.: 29322980
• European Community (EC) Number: 207-839-3
• NSC Number: 197009,51296
• UNII: 8KXK25H388
• DSSTox Substance ID: DTXSID7075422
• Nikkaji Number: J82.323F,J3.297.931I
• Wikidata: Q4596886
• Metabolomics Workbench ID: 45434
• ChEMBL ID: CHEMBL166223
• Mol file: 497-23-4.mol

Synonyms:2-B4O;2-buten-4-olide;2-furanone;butenolide;crotonolactone

Chemical Property of 2(5H)-Furanone

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 0.273mmHg at 25°C
• Melting Point: 4-5 °C(lit.)
• Refractive Index: n20/D 1.469(lit.)
• Boiling Point: 203.7 °C at 760 mmHg
• Flash Point: 87.3 °C
• PSA: 26.30000
• Density: 1.209 g/cm³
• LogP: 0.09940
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate (Slightly)
• Water Solubility.: Immiscible with water.
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 84.021129366
• Heavy Atom Count: 6
• Complexity: 93.7

Purity/Quality:

99% ^*data from raw suppliers

2-Furanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C=CC(=O)O1
• 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. 2(5H)-Furanone is a heterocyclic organic compound that is used widely in the synthetic preparation of pharmaceutical goods. 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

Technology Process of 2(5H)-Furanone

There total 239 articles about 2(5H)-Furanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(E/Z)-trimethylsilyl 4-bromo-2-butenoate → trimethylsilyl bromide (2857-97-8) + 2-buten-4-olide (497-23-4)

Guidance literature:

at 140 - 170 ℃; for 1h;

Reference yield: 76.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + silver trifluoroacetate (2966-50-9) → 5-butylfuran-2(5H)-one (30336-14-2,70404-04-5) + n-butyl trifluoroacetate (367-64-6) + 2-buten-4-olide (497-23-4) + 3-butylfuran-2(3H)-one (124083-30-3)

Guidance literature:

With 1-iodo-butane; In dichloromethane; Further byproducts given. Title compound not separated from byproducts; 1.) -78 deg C, 2.) to 10 deg C, 4 h;

DOI:10.1002/hlca.19890720625

Reference yield: 76.0%

1-iodo-butane (542-69-8) + (furan-2-yloxy)-trimethylsilane (61550-02-5) + silver trifluoroacetate (2966-50-9) → 5-butylfuran-2(5H)-one (30336-14-2,70404-04-5) + n-butyl trifluoroacetate (367-64-6) + 4-oxo-octanoic acid butyl ester (18688-70-5) + 2-buten-4-olide (497-23-4)

Guidance literature:

In dichloromethane; Further byproducts given. Title compound not separated from byproducts; 1.) -78 deg C, 2.) to 10 deg C, 4 h;

DOI:10.1002/hlca.19890720625

upstream raw materials:

4-Hydroxy-dihydro-furan-2-on

(Z)-4-chlorobut-2-ene nitrile

(E)-4-chlorobut-2-enoic acid

4-hydroxy-2-butynoic acid

Downstream raw materials:

4-[2'-(1'',3''-benzodioxol-5''-yl)-1',3'-dithian-2'-yl]dihydro-2(3H)-furanone

2-(4-benzyloxy-3-methoxybenzyl)-3-(3,4-methylenedioxybenzoylpropane-1,3-dithiane)-γ-butyrolactone

(3R,4S)-4-(2-Benzo[1,3]dioxol-5-yl-[1,3]dithian-2-yl)-3-[hydroxy-(2,3,4-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

4-(4-methoxyphenyl)furan-2(5H)-one

Refernces

• 1、 Takano,Ogasawara. "-". . p. 42. Retrieved 1974.
• 2、 Gassama, Abdoulaye,Ernenwein, Cedric,Hoffmann, Norbert. "Synthesis of surfactants from furfural derived 2[5H]-furanone and fatty amines". . p. 859 - 865. Retrieved 2010.
• 3、 Boden. "-". . p. 143. Retrieved 1978.
• 4、 Smith,Jones. "-". . p. 2092. Retrieved 1959.
• 5、 Badovskaya. "-". . . Retrieved 1978.
• 6、 Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang. "Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal". . . Retrieved 2021/09/28.
• 7、 Zhao, Xin,Kong, Xiangpeng,Wang, Fengliang,Fang, Ruiqi,Li, Yingwei. "Metal Sub-nanoclusters Confined within Hierarchical Porous Carbons with High Oxidation Activity". supporting information. p. 10842 - 10849. Retrieved 2021/03/16.