2-Methyltetrahydrofuran-3-one

Base Information

• Chemical Name: 2-Methyltetrahydrofuran-3-one
• CAS No.: 3188-00-9
• Deprecated CAS: 159551-39-0
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29329990
• European Community (EC) Number: 221-685-4
• UNII: I3703CL967
• DSSTox Substance ID: DTXSID9047677
• Nikkaji Number: J75.503F
• Wikipedia: Coffee_furanone
• Wikidata: Q3885889
• Metabolomics Workbench ID: 44727
• ChEMBL ID: CHEMBL3188615
• Mol file: 3188-00-9.mol

Synonyms:2-methyltetrahydrofuran-3-one

Chemical Property of 2-Methyltetrahydrofuran-3-one

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 6.56mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Boiling Point: 139 °C at 760 mmHg
• Flash Point: 53.7 °C
• PSA: 26.30000
• Density: 1.04 g/cm³
• LogP: 0.36430
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 88.1

Purity/Quality:

98% ^*data from raw suppliers

2-Methyltetrahydrofuran-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, Xi
• Hazard Codes: Xn,T,Xi
• Statements: 10-22-36/37/38-2017/10/2
• Safety Statements: 16-26-36/37/39-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)CCO1
• Description: 2-Methyltetrahydrofuran-3-one has a bread, buttery topnote. May be prepared by hydrolytic decarboxylation of 2-methyl-4-carbomethoxytetrahydrofuran- 3-one; by acid-catalyzed ring closure of p-alkoxy- diazoketones.
• Uses: 2-Methyltetrahydro-3-furanone has been employed as an quorum sensing inhibitor-molecule to investigate its effect on growth and biofilm formation in Hafnia alvei.

Technology Process of 2-Methyltetrahydrofuran-3-one

There total 12 articles about 2-Methyltetrahydrofuran-3-one 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: 55.2%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7,594837-91-9,98634-97-0,313643-49-1) → 2-methyltetrahydrofuran-3-one (3188-00-9)

Guidance literature:

With borax; Oxone; sodium hydroxide; sodium tetraborate decahydrate; In water; at 20 - 25 ℃; for 3h; pH=8.5;

DOI:10.1080/00397919809458708

Reference yield:

vitamin C (50-81-7,98966-42-8) → 1-(2-furyl)-1-ethanone (1192-62-7,80145-44-4) + cyclohexenone (930-68-7) + 2-methyltetrahydrofuran-3-one (3188-00-9) + 2-hydroxy-2-cyclopenten-1-one (10493-98-8) + 4-methylcyclopent-2-en-1-one (23033-96-7) + dimethylglyoxal (431-03-8)

Guidance literature:

at 300 ℃; for 0.05h; dry degradation; degradation under milder condition;

DOI:10.1016/S0008-6215(97)00234-6

Reference yield:

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (28564-83-2) → furaneol (3658-77-3,192466-95-8) + 5-hydroxymaltol (1073-96-7) + 2-methyltetrahydrofuran-3-one (3188-00-9) + 2,3-Pentanedione (600-14-6) + 2-hydroxy-3-methylcyclopent-2-en-1-one (80-71-7) + hydroxy-2-propanone (116-09-6)

Guidance literature:

With water; at 150 ℃; for 1h; also 2,3-dihydro-3,5-dihydroxy-6(¹³C)methyl-4(H)-pyran-4-one; var. temp., pH, and time; effect of 2,4-dihydroxy-2,5-dimethyl-3(2H)-furanone;

DOI:10.1021/jf950208h

upstream raw materials:

1-Methyl-2-oxa-6,10-dithia-spiro[4.5]decane

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

vitamin C

3-acetyl-2-oxo-4,5-dihydrofuran

Downstream raw materials:

[2-Methyl-dihydro-furan-(3E)-ylidene]-((R)-1-phenyl-ethyl)-amine

[2-Methyl-dihydro-furan-(3E)-ylidene]-((R)-1-phenyl-ethyl)-amine

(3S*)-hydroxy-(2S*)-methyltetrahydrofuran

2-methyltetrahydrofuran-3-amine

Refernces

• 1、 Cerny, Christoph,Briffod, Matthieu. "Effect of pH on the maillard reaction of [C]xylose, cystein, and thiamin". scheme or table. p. 1552 - 1556. Retrieved 2009/10/01.
• 2、 Kim, Myong-Ock,Baltes, Werner. "On the Role of 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one in the Maillard Reaction". . p. 282 - 289. Retrieved 2007/10/03.