78948-09-1

Basic information

• Product Name: acetyl hypofluorite
• Synonyms: acetyl hypofluorite
• CAS NO: 78948-09-1
• Molecular Formula: C₂H₃FO₂
• Molecular Weight: 78.04
• Mol File: 78948-09-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: -96 °C
• Boiling Point: 19.9°C at 760 mmHg
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 920mmHg at 25°C
• Refractive Index: 1.301
• CAS DataBase Reference: acetyl hypofluorite(CAS DataBase Reference)
• NIST Chemistry Reference: acetyl hypofluorite(78948-09-1)
• EPA Substance Registry System: acetyl hypofluorite(78948-09-1)

Safety Data

• Hazardous Substances Data: 78948-09-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C2H3FO2/c1-2(4)5-3/h1H3

Upstream product

• 64-19-7 acetic acid 
• 127-08-2 potassium acetate 
• 127-09-3 sodium acetate 
• 97984-89-9 sodium dihydrogen triacetate 

Downstream Products

• 109-09-1 2-chloropyridine 
• 3847-19-6 2-acetoxypyridine 
• 109-04-6 2-bromo-pyridine 
• 115923-81-4 Acetic acid 5,5-difluoro-1-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 115923-75-6 Acetic acid (4S,5R)-5-fluoro-1-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 115923-75-6 Acetic acid (4S,5S)-5-fluoro-1-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 4840-69-1 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione 
• 372-46-3 fluorocyclohexane 
• 622-45-7 cyclohexyl acetate 
• 82166-21-0 methyl cyclohexane 
• 110-83-8 cyclohexene 
• 98014-25-6 cis-1-acetoxy-2-fluorocyclohexane 
• 433305-07-8 trans-1-acetoxy-2-fluorocyclohexane 
• 139161-94-7 4-chloro-3,5-difluoro-2-picoline 

Relevant articles and documents

Two-step regio- and stereoselective syntheses of [19F]- and [18F]-2-deoxy-2-(R)-fluoro-β-D-allose

Replacement of specific hydroxyl groups by fluorine in carbohydrates is an ongoing challenge from chemical, biological, and pharmaceutical points of view. A rapid and efficient two-step, regio- and stereoselective synthesis of 2-deoxy-2-(R)-fluoro-β-d-allose (2-(R)-fluoro-2-deoxy-β-d-allose; 2-FDβA), a fluorinated analogue of the rare sugar, d-allose, is described. TAG (3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-d-arabino-hex-1-enitol or 3,4,6-tri-O-acetyl-d-glucal), was fluorinated in anhydrous HF with dilute F 2 in a Ne/He mixture or with CH3COOF at -60°C. The fluorinated intermediate was hydrolyzed in 1 N HCl and the hydrolysis product was purified by liquid chromatography and characterized by 1D 1H, 13C, and 19F NMR spectroscopy as well as 2D NMR spectroscopy and mass spectrometry. In addition, 18F-labeled 2-deoxy-2-(R)-fluoro-β-d-allose (2-[18F]FDβA) was synthesized for the first time, with an overall decay-corrected radiochemical yield of 33 ± 3% with respect to [18F]F2, the highest radiochemical yield achieved to date for electrophilic fluorination of TAG. The rapid and high radiochemical yield synthesis of 2-[18F] FDβA has potential as a probe for the bioactivity of D-allose.

Activation of a CH bond in polypyridine systems by acetyl hypofluorite made from F2

Activation of the relatively inactive polypyridine backbone with strong electrophilic fluorine, originating from acetyl hypofluorite (AcOF) enables attack of the acetoxy moiety at the α position to the heteroatom. Derivatives of bipyridine, phenanthroline and terpyridine systems have been acetoxylated or oxygenated within a few minutes usually in very good yields.

Mono and difluorination of centers α to sulfonates and phosphonates using AcOF

Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties CH2SO2 or COCH2PO react with bases to create the corresponding anions wh