81189-55-1

Basic information

• Product Name: 4-(ACETOXYMETHYL)-2-FURANONE
• Synonyms: 4-(ACETOXYMETHYL)-2(5H)-FURANONE
• CAS NO: 81189-55-1
• Molecular Formula: C7H8O4
• Molecular Weight: 156.136
• Mol File: 81189-55-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 303.7°Cat760mmHg
• Flash Point: 159.6°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 0.000913mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: 4-(ACETOXYMETHYL)-2-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(ACETOXYMETHYL)-2-FURANONE(81189-55-1)
• EPA Substance Registry System: 4-(ACETOXYMETHYL)-2-FURANONE(81189-55-1)

Safety Data

• Hazardous Substances Data: 81189-55-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H8O4/c1-5(8)10-3-6-2-7(9)11-4-6/h2H,3-4H2,1H3

Upstream product

• 61934-55-2 3-bromomethyl-2-butenolide 
• 127-08-2 potassium acetate 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 
• 860374-03-4 acetic acid 2,5-dioxo-2,5-dihydro-furan-3-ylmethyl ester 
• 4167-06-0 2-bromo-2-(bromomethyl)succinic acid 
• 541-47-9 3-Methylbutenoic acid 
• 127-09-3 sodium acetate 
• 75887-43-3 4-bromo-3-(bromomethyl)but-2-enoic acid 

Downstream Products

• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 125973-97-9 4-formylfuran-1(5H)-one 
• 133435-76-4 4-(benzyloxymethyl)-2(5H)-furanone 
• 172796-28-0 (R)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one 
• 133435-77-5 (S)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one 
• 1620754-39-3 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (5-oxotetrahydrofuran-3-yl)methyl carbonate 
• 36679-81-9 4-hydroxymethyl-1,2,3,4-tetrahydrofuran-2-one 

Relevant articles and documents

Parallel synthesis: A new approach for developing analytical internal standards. Application to the analysis of patulin by gas chromatography-mass spectrometry

The polymer-assisted reaction of 4-(hydroxymethyl)furan-2(5H)-one (4HM2F) with 21 carboxylic acids using polystyrene-carbodiimide (PS-carbodiimide) yielded an ester library. Four of the esters, (5-oxo-2,5-dihydrofuran-3-yl) methyl acetate (IS-1), (5-oxo-2

Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry

Fragmentation reactions of β-hydroxymethyl-, β-acetoxymethyl- and β-benzyloxymethyl-butenolides and the corresponding γ-butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) using collision-induced dissociation (CID). This study revealed that loss of H2O [M+H-18]+ is the main fragmentation process for β-hydroxymethylbutenolide (1) and β-hydroxymethyl-γ- butyrolactone (2). Loss of ketene ([M+H-42]+) is the major fragmentation process for protonated β-acetoxymethyl-γ-butyrolactone (4), but not for β-acetoxymethylbutenolide (3). The benzyl cation (m/z 91) is the major ion in the ESI-MS/MS spectra of β-benzyloxymethylbutenolide (5) and β-benzyloxymethyl-γ-butyrolactone (6). The different side chain at the β-position and the double bond presence afforded some product ions that can be important for the structural identification of each compound. The energetic aspects involved in the protonation and gas-phase fragmentation processes were interpreted on the basis of thermochemical data obtained by computational quantum chemistry. Copyright

From tetronic acid and furfural to C(4)-halogenated, vinylated and formylated furan-2(5H)-ones and their 5-alkoxy derivatives

Tetronic acid and furfural have been elaborated into the title compounds. Palladium-catalyzed cross coupling with vinylstannanes and controlled ozonolysis followed by anhydrous workup are key reactions.