5-Methylfuran-3(2H)-one

Base Information

• Chemical Name: 5-Methylfuran-3(2H)-one
• CAS No.: 3511-32-8
• Molecular Formula: C5H6 O2
• Molecular Weight: 98.1014
• Hs Code.: 2932190090
• UNII: D0380N8E30
• DSSTox Substance ID: DTXSID30188608
• Nikkaji Number: J150.443F
• Wikidata: Q27275917
• Mol file: 3511-32-8.mol

Synonyms:5-Methylfuran-3(2H)-one;3511-32-8;5-Methylfuran-3-one;3(2H)-furanone, 5-methyl-;5-METHYL-3(2H)-FURANONE;FEMA no. 4176;5-Methyl-3(2H)-furanone [FHFI];D0380N8E30;5-methyl-furan-3-one;3(2H)-Furanone,5-methyl-;UNII-D0380N8E30;DTXSID30188608;DFZCBMOGIYUCLI-UHFFFAOYSA-N;5-methyl-2,3-dihydrofuran-3-one;MFCD15143719;AKOS022174770;AS-58431;CS-0092875;NS00120974;Y10351;A874762;Q27275917

Chemical Property of 5-Methylfuran-3(2H)-one

Chemical Property:

• Vapor Pressure: 2.121mmHg at 25°C
• Refractive Index: 1.4945 (20℃)
• Boiling Point: 60℃ (12 Torr)
• Flash Point: 61.7±15.3℃
• PSA: 26.30000
• Density: 1.120±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 0.48950
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 124

Purity/Quality:

97% ^*data from raw suppliers

5-Methylfuran-3(2H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)CO1
• General Description: 5-Methyl-3(2H)-furanone is a highly reactive compound that readily undergoes reactions with Schiff bases under acidic conditions, leading to the stereospecific formation of 5-styryl-3(2H)-furanone derivatives. Its reactivity is demonstrated in the synthesis of (Z)-2-benzylidene-4-ethoxycarbonyl-3-oxo-5-(E)-styryl-2,3-dihydrofurans when reacted with imines, highlighting its utility in constructing complex furanone-based structures. 3(2H)-Furanone, 5-methyl-'s versatility is further evidenced by its ability to form intermediates for subsequent reactions with different Schiff bases, making it a valuable building block in synthetic chemistry.

Technology Process of 5-Methylfuran-3(2H)-one

There total 8 articles about 5-Methylfuran-3(2H)-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: 100.0%

1-bromo-2,4-dioxopentane (64454-96-2) → 5-methyl-3(2H)-furanone (3511-32-8)

Guidance literature:

With potassium carbonate; In diethyl ether; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2007.03.166

Reference yield: 80.0%

C5H9NO2 → 5-methyl-3(2H)-furanone (3511-32-8)

Guidance literature:

C₅H₉NO₂; With hydrogenchloride; In water; pH=< 1;

With sodium hydrogencarbonate; In water;

DOI:10.1080/00397910903047778

Reference yield: 54.0%

4-Methoxy-4-(2,2-dimethoxypropyl)-1,3-dioxolan (79923-36-7) → 5-methyl-3(2H)-furanone (3511-32-8)

Guidance literature:

With toluene-4-sulfonic acid; trimethyl orthoformate; 1.) methanol, room temp., 36 h, 2.) H₂O, room temp., 24 h;

DOI:10.1055/s-1981-29582

upstream raw materials:

4-Methoxy-4-(2,2-dimethoxypropyl)-1,3-dioxolan

3-chloroacetyl acetone

1-bromo-2,4-dioxopentane

(Z)-2,2,4,8,8-pentamethyl-6-methylene-3,7-dioxa-2,8-disilanon-4-ene

Downstream raw materials:

inotilone

2-[bis-(3-keto-5-methylfuranyl)]-3,5-di-tert-butyl-4-hydroxyphenylmethane

2-(2,4-dihydroxybenzylidene)-5-methylfuran-3-one

3-methyl-5-isoxazolemethanol

Refernces

Reactivity of 5-Methyl-3(2H)-furanones toward Schiff Bases; Synthesis of 5-Styryl-3(2H)-furanone Derivatives

10.1055/s-1981-29328

The research investigates the reactivity of 5-methyl-3(2H)-furanones towards Schiff bases, aiming to synthesize 5-styryl-3(2H)-furanone derivatives. The study demonstrates that the reaction of Schiff bases with ketones, which is formally analogous to the aldol reaction, is feasible under acidic conditions. Key chemicals used include 4-ethoxycarbonyl-5-methyl-3-oxo-2,3-dihydrofuran (1), various imines (2), and acetic acid. The researchers found that the reaction proceeds stereospecifically to form (Z)-2-benzylidene-4-ethoxycarbonyl-3-oxo-5-(E)-styryl-2,3-dihydrofurans (3) when two mol equivalents of imines are used. For compounds with different aryl groups, an intermediate (4) is first prepared and then reacted with a second Schiff base. The study concludes that the 5-methyl-3(2H)-furanone system exhibits high reactivity, and the synthesized compounds' structures are confirmed by microanalyses and spectral data.