14400-67-0

Basic information

• Product Name: 2,5-Dimethyl-3(2H)-furanone
• Synonyms: 2,5-dimethyl-3(2h)-furanon;2H-Furan-3-one, 2,5-dimethyl;FEMA 4101;2,3-DIHYDRO-2,5-DIMETHYL-3-FURANONE;2,5-DIMETHYLFURAN-3(2H)-ONE;2,5-DIMETHYL-2,3-DIHYDROFURAN-3-ONE;2,5-Dimethyl-2H-furan-3-one;3(2H)-Furanone, 2,5-dimethyl-
• CAS NO: 14400-67-0
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13
• EINECS: 238-365-5
• Product Categories: Furans, Benzofurans & Dihydrobenzofurans;furnan Flavor;Furans, Benzofurans & Dihydrobenzofurans
• Mol File: 14400-67-0.mol

Chemical Properties

• Boiling Point: 259-261°C
• Flash Point: 259-261°C
• Appearance: yellow liquid
• Density: 1.06
• Vapor Pressure: 1.55mmHg at 25°C
• Refractive Index: 1.4770 to 1.4810
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,5-Dimethyl-3(2H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethyl-3(2H)-furanone(14400-67-0)
• EPA Substance Registry System: 2,5-Dimethyl-3(2H)-furanone(14400-67-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• RIDADR: UN3271
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 14400-67-0(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
2,5-Dimethyl-3(2H)-furanone is used as a flavoring agent for its caramellic type aroma. It is particularly effective in enhancing the taste of various food products, such as baked goods, confectionery, and beverages, by adding a rich, sweet, and complex flavor profile.
Used in Fragrance Industry:
In the fragrance industry, 2,5-Dimethyl-3(2H)-furanone is used as a fixative agent to help stabilize and prolong the scent of perfumes and other fragrance products. Its fruity ester notes add a pleasant and versatile aroma, making it suitable for a wide range of fragrance applications.
Used in Aromatherapy:
Due to its high strength odor and pleasant aroma, 2,5-Dimethyl-3(2H)-furanone can be used in aromatherapy as a component in essential oil blends. It may help create a relaxing and comforting atmosphere, promoting a sense of well-being and reducing stress.

InChI:InChI=1/C6H8O2/c1-4-3-6(7)5(2)8-4/h3,5H,1-2H3/t5-/m1/s1

Upstream product

• 57556-12-4 3-methoxy-2,5-dimethyl-furan 
• 61892-85-1 3-hydroxyhexane-2,5-dione 
• 15441-67-5 5-hydroxyhex-3-yn-2-one 
• 124-38-9 carbon dioxide 
• 431-03-8 dimethylglyoxal 
• 71502-43-7 (3-methyl-5-isoxazolyl)-1-ethanol 
• 105653-96-1 4,4-Dimethoxy-2,5-dimethyl-tetrahydro-furan-2-ol 
• 3031-66-1 3-hexyn-2,5-diol 
• 17492-61-4 1-(3-methyl-4,5-dihydro-isoxazol-5-yl)-ethanone 
• 55086-61-8 5-acetyl-3-methylisoxazole 
• 14400-69-2 2-hydroxymethyl-2,5-dimethyl-furan-3-one 

Downstream Products

• 52204-42-9 2,2'-(m-phenylene)-bis(3-methyl-3-pyrazolin-5-one) 

Relevant articles and documents

A NEW REACTION OF ACETYLENES, THE ADDITION OF METHANOL TO 5-HYDROXYHEX-3-YN-2-ONE. SYNTHESIS OF THE "ONION FURANONE", 2-HEXYL-5-METHYL-3-FURANONE.

The conversion of alkyl-substituted 4-hydroxybut-2-ynones to 2,5-dialkyl-3-furanones via 2,5-dialkyl-methoxyfurans is described.

An Unusual Substitution Reaction in a Benzotetrazine Derivative

1-Methyl-3H-pyrazolobenzotetrazin-3-one decomposes in alcohols, with loss of nitrogen and intramolecular hydrogen transfer, to form 5-alkoxymethyl-1,2-dihydro-1-phenyl-3H-pyrazol-3-ones.

Further enolate alkylation studies of 2,5-dimethyl-3(2H)-furanone

Heterocyclic ketones, such as 2,5-dimethyl-3(2H)-furanone, provide multifunctional intermediates to various compounds. One property of these that has proven useful is the ability to alkylate the γ′-position of the dienolate. This report demonstrates the versatility of γ′-dienolate substitutions as employed toward syntheses of certain natural products and highly reactive electrophiles provide the best substrates for efficient substitution.

New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity

A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety.

New Syntheses of Geiparvarin and 2,5-Dimethyl-3(2H)-furanone via CO2 Mediated Bond Reorganization

A new synthesis of 3(2H)-furanones from 4-hydroxy-2-alkyn-1-one derivatives via CO2 mediated bond reorganization has been developed to the preparation of an antitumor agent, geiparvarin and a constituent of flavors, 2,5-dimethyl-3(2H)-furanone.

Silyl Nitronates in Organic Synthesis. Routes to Heterocycles and Cyclopentanoids. Synthesis of Allethrolone and Calythrone. Acylation and Cyanohydroxylation of Double Bonds. An Exploratory Study

Silyl nitronates are versatile reagents for the preparation of heterocycles by dipolar addition to double bonds.The intermediate isoxazolidines can be transformed to 2-isoxazolines, isoxazoles, furans, dihydrofuranones, pyrazoles, pyridazines and pyridazones.Reduction of 2-isoxazolines with Ti3+ leads to hydroxylated 1,4-diketones, which subsequently can be cyclized to cyclopentenones.Routes to calythrone, rethrolones, prostanoids and a number of naturally occurring dihydrofuranones are devised, as well as synthetic procedures for acylation, preparation of endiones, hydroxyacylation, cyanation and hydroxycyanation of double bonds.

Process for preparing 2,5-dimethyl-3-(2H)-furanone

There is disclosed a simple, economical process for preparing 2,5-dimethyl-3-(2H)-furanone by hydrolysis of the dimer of diacetyl at a temperature of 20°C to 120°C and in the presence of an acid, mineral or organic, or of a cationic resin, with elimination of a acetic acid.