5584-69-0

Basic information

• Product Name: 3,5-dimethylfuran-2(5H)-one
• Synonyms: 2(5H)-furanone, 3,5-dimethyl-; 2-Furanone, 2,5-dihydro-3,5-dimethyl
• CAS NO: 5584-69-0
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.1265
• Mol File: 5584-69-0.mol

Chemical Properties

• Boiling Point: 218.5°C at 760 mmHg
• Flash Point: 81.2°C
• Density: 1.042g/cm³
• Vapor Pressure: 0.125mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: 3,5-dimethylfuran-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-dimethylfuran-2(5H)-one(5584-69-0)
• EPA Substance Registry System: 3,5-dimethylfuran-2(5H)-one(5584-69-0)

Safety Data

• Hazardous Substances Data: 5584-69-0(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 74785-05-0 (Z)-4-iodopent-3-en-2-ol 
• 100289-56-3 4-methyl-4-(1-propenyl)malonyl peroxide 
• 57984-70-0 Pent-3-yn-2-ol 
• 78196-34-6 but-3-en-2-yl methacrylate 
• 98315-06-1 (5S)-4-hydroxy-3,5-dimethyl-2(5H)-furanone 
• 3740-58-7 2,4-dimethyl-Δ3-γ-butyrolactone 
• 24642-00-0 ethyl 2-methylpenta-2,3-dienoate 
• 20459-96-5 2-Methyl-4-pentensaeuremethylester 
• 123-54-6 acetylacetone 
• 122693-49-6 (2R,4S)-4-Hydroxy-5-imino-2,4-dimethyl-tetrahydro-furan-2-carbonitrile 
• 122693-56-5 (2R,4S)-4-Hydroxy-2,4-dimethyl-5-oxo-tetrahydro-furan-2-carbonitrile 
• 85287-81-6 3,5-Dimethyl-4-phenylsulfanyl-dihydro-furan-2-one 
• 89609-42-7 7-methyl-1,4-dioxaspiro<2.4>heptan-5-one 

Relevant articles and documents

A convenient method for lactonization of α-allyl esters using iodine in dimethylsulphoxide

A simple method for the synthesis of α-γ-disubstituted-γ-butyrolactones by cyclization of α-allyl esters using iodine in dimethylsulphoxide is reported. This method is efficient and operationally simple in comparison to methods using transition metal comp

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

Volatiles released by the marine Roseobacter clade bacterium Rugeria pomeroyi were collected by use of a closed-loop stripping headspace apparatus (CLSA) and analysed by GC-MS. Several lactones were found for which structural proposals were derived from their mass spectra and unambiguously verified by the synthesis of reference compounds. An enantioselective synthesis of two exemplary lactones was performed to establish the enantiomeric compositions of the natural products by enantioselective GC-MS analyses. The lactones were subjected to biotests to investigate their activity against several bacteria, fungi, and algae. A specific algicidal activity was observed that may be important in the interaction between the bacteria and their algal hosts in fading algal blooms.

Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule

An unprecedented enantioselective and general olefin isomerization was realized via biomimetic proton transfer catalysis with a new chiral organic catalyst. A broad range of mono- and disubstituted β,γ-unsaturated butenolides were transformed into the corresponding chiral α,β- unsaturated butenolides in high enantioselectivity and yield in the presence of as low as 0.5 mol % catalyst. Mechanistic studies have revealed the protonation as the rate-determining step.

SYSTEM AND METHOD FOR CONTROLLING GROWTH OF MICROORGANISMS WITH BROMINATED FURANONES

A method for inhibiting the growth of a microorganism using an effective amount of one or more of the following synthetic brominated furanones: (i) 4-bromo-5Z-(bromomethylene)-3-methylfuran-2-one; (ii) 3-(dibromomethyl)-5-(dibromomethylene)furan-2-one; (iii) 3-(bromomethyl)-5-(dibromomethylene)furan-2-one; (iv) 4-bromo-3-(bromomethyl)-5Z-(bromomethylene)furan-2-one; or (v) 4-bromo-5-(dibromomethyl)-3-methylfuran-2(5H)-one. The brominated furanones inhibit the growth of both fungi and bacteria, including the fungal species Candida albicans, Gloeophyllum trabeum, Chaetomium globosum, and Trametes versicolor and the bacterial species Pseudomonas aeruginosa. The brominated furanones can be used topically or internally to treat human infections, and can be used to treat other objects, such as wood building supplies, to prevent fungal rot.

A general synthetic approach to 5-alkyl-2(5H)furanones via 1,3-dipolar cycloaddition

[3+2] Cycloaddition methodology provides a general and efficient access to 5-alkyl substituted 2(5H)furanones. The synthetic approach has been exploited towards the synthesis of naturally occurring butenolides.

Palladium-Catalyzed Cyclocarbonylation of Terminal and Internal Alkynols to 2(5H)-Furanones

A series of substituted alkynols, containing alkyl, phenyl, and vinyl groups at the acetylenic terminal, were found to undergo direct carbonylation to the corresponding substituted 2(5H)-furanones in 67-98% yield. This reaction requires catalytic quantiti

An Efficient and Versatile Synthesis of the Butenolide Subunit of 4-Hydroxylated Annonaceous Acetogenins

Title butenolides 2 have been synthesized by an efficient and versatile route that provides access to any stereoisomer by use of individual enantiomers of the precursors 3-butyn-2-ol and terminal epoxides.

Preparation of α-Hydroxy-γ-lactones and their Application in the Synthesis of α,β-Butenolides, α-Alkylidene-γ-lactones and Furans

A straightforward synthesis of α-hydroxy-γ-butyrolactones was carried out by condensation reaction of the lithium anion of ethoxyethyl-protected cyanohydrins with epoxides, followed by acidic treatment.Synthetic applications of these synthons in the preparation of interesting α,β-butenolides, α-alkylidene-γ-lactones and furans are described.

Synthesis of the C5-C9 Fragment of the Polypropionate Unit of the Geodiamolides and Jaspamide

An alternative stereoselective approach to the C5-C9 fragment of the polypropionate unit of the geodiamolide and jaspamide is described.