5-Methyl-2(5H)-furanone

Base Information

• Chemical Name: 5-Methyl-2(5H)-furanone
• CAS No.: 591-11-7
• Molecular Formula: C5H6 O2
• Molecular Weight: 98.1014
• European Community (EC) Number: 209-700-2
• NSC Number: 11835,655
• UNII: 1AX0NCS144
• DSSTox Substance ID: DTXSID901014526
• Nikkaji Number: J13.667K
• Wikidata: Q27116831
• ChEMBL ID: CHEMBL47969
• Mol file: 591-11-7.mol

Synonyms:alpha-angelicalactone;angelica lactone;angelica lactone, (alpha)-isomer;angelica lactone, (beta)-isomer

Chemical Property of 5-Methyl-2(5H)-furanone

Chemical Property:

• Vapor Pressure: 0.197mmHg at 25°C
• Melting Point: <-17 °C
• Refractive Index: 1.4454
• Boiling Point: 210°C at 760 mmHg
• Flash Point: 78.9°C
• PSA: 26.30000
• Density: 1.095g/cm³
• LogP: 0.48790
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 115

Purity/Quality:

99% ^*data from raw suppliers

5-?Methylfuran-?2(5H)?-?one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC(=O)O1
• Uses: 5-?Methylfuran-?2(5H)?-?one can be used in analytical study of improved molecular level identification of organic compounds using comprehensive two-?dimensional chromatography, dual ionization energies and high resolution mass spectrometry.

Technology Process of 5-Methyl-2(5H)-furanone

There total 70 articles about 5-Methyl-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: 95.0%

carbon monoxide (201230-82-2) + (2R*,3Z)-4-Iodo-3-buten-2-ol (74785-04-9) → 5-methyl-5H-furan-2-one (591-11-7)

Guidance literature:

With potassium carbonate; hydrazine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 35 ℃; for 72h; under 2280 Torr;

DOI:10.1021/ja00532a034

Reference yield: 93.0%

(E)-3-pentenoic acid (1617-32-9) → 5-methyl-5H-furan-2-one (591-11-7)

Guidance literature:

(E)-3-pentenoic acid; With Oxalyl bromide; dimethyl sulfoxide; In dichloromethane; at -10 - 20 ℃; for 1.16667h; Inert atmosphere;

With potassium carbonate; In dichloromethane-d2; water; at 20 ℃; for 5h; Inert atmosphere;

Reference yield: 93.0%

3-pentenoic acid (5204-64-8) → 5-methyl-5H-furan-2-one (591-11-7)

Guidance literature:

3-pentenoic acid; With Oxalyl bromide; dimethyl sulfoxide; In dichloromethane; at -10 - 20 ℃; Inert atmosphere;

With sodium hydroxide; In dichloromethane; water; for 5h; Reagent/catalyst;

DOI:10.1080/00397911.2019.1652914

upstream raw materials:

5-methyl-2-furanone

triethylamine

levulinic acid

5-hydroxy-2-(5H)-furanone

Downstream raw materials:

4-(2,5-Dimethylphenyl)valeriansaeure

4-p-tolylpentanoic acid

4-m-tolyl-valeric acid

5-methyl-2-furanone

Refernces

• 1、 Lu, Boqiong,Li, Jinlong,Lv, Guangqiang,Qi, Yongqin,Wang, Yingxiong,Deng, Tiansheng,Hou, Xianglin,Yang, Yongxing. "Obtaining a high value branched bio-alkane from biomass-derived levulinic acid using RANEY as hydrodeoxygenation catalyst". . p. 93956 - 93962. Retrieved 2016.
• 2、 Zhuo, Kai-Feng,Yu, Shang-Hai,Gong, Tian-Jun,Fu, Yao. "Regioselective β-Arylation of α-Angelica Lactone through Isomerization/Addition under Mild Conditions". . p. 693 - 697. Retrieved 2020.
• 3、 Chowdhury, Somak,Klapper, Martin,Menzel, Klaus-Dieter,Paschold, André,Rosenbaum, Miriam A.,Schlabach, Kevin,Stallforth, Pierre,Zhang, Shuaibing. "Biosynthesis of Pseudomonas-Derived Butenolides". supporting information. p. 5607 - 5610. Retrieved 2020/02/04.
• 4、 Hong, Miao,Wang, Xiao-Jun. "Lewis-Pair-Mediated Selective Dimerization and Polymerization of Lignocellulose-Based β-Angelica Lactone into Biofuel and Acrylic Bioplastic". supporting information. p. 2664 - 2668. Retrieved 2020/01/24.