36336-08-0

Basic information

• Product Name: Hypofluorous acid, methyl ester (9CI)
• Synonyms: Methylhypofluorite
• CAS NO: 36336-08-0
• Molecular Formula: CH₃FO
• Molecular Weight: 50.0323
• Mol File: 36336-08-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 0.879g/cm³
• CAS DataBase Reference: Hypofluorous acid, methyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Hypofluorous acid, methyl ester (9CI)(36336-08-0)
• EPA Substance Registry System: Hypofluorous acid, methyl ester (9CI)(36336-08-0)

Safety Data

• Hazardous Substances Data: 36336-08-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 

Downstream Products

• 132803-35-1 1,1-diphenyl-1-fluoro-2-methoxyethane 
• 61840-84-4 2-methoxy-4-methylcyclohexanone 
• 35394-07-1 4-tert-butyl-2-methoxycyclohexanone 
• 156479-56-0 1-fluoro-2-methoxy-1,2-diphenylethane 
• 65915-91-5 1-ethoxymethyl-2,3,4,5,6-pentamethyl-benzene 
• 4079-52-1 methoxymethyl phenyl ketone 
• 143191-51-9 1-phenyl-1,1,2-trimethoxyethane 
• 14337-37-2 2,3,5,6-tetramethylanisole 
• 425-88-7 1,1,2,2-tetrafluoro-1-methoxyethane 
• 50285-05-7 (1,2,2,2-tetrafluoroethyl)methyl ether 
• 428-66-0 1,1,2-Trifluoroethyl methyl ether 
• 460-43-5 2,2,2-trifluoroethyl methyl ether 
• 461-57-4 2,2-difluoroethyl methyl ether 
• 375-03-1 heptafluoropropyl methyl ether 

Relevant articles and documents

The Chemistry of Methyl Hypofluorite: Its Reactions with Various Unsaturated Centers

Methyl hypofluorite was until recently grouped as a hypothetical member of those smallest organic molecules which had not been synthesized.Passing F2 through a solution of methanol in MeCN or PrCN resulted in this successful preparation.MeOF is an unique reagent, since it generates the novel electrophilic methoxylium moiety in contrast to the much more common methoxide group.This hypofluorite was reacted with several types of olefins including benzylic, cyclic, bicyclic, straight chain, and steroidal ones.In most cases the regioselectivity is very good, reflecting the unique polarization of the reagent: MeOδ(+)Fδ(-).The stereoselectivity tends to be less emphasized, but usually anti addition is dominant.

A novel electrophilic methoxylation (with a little help from F2)

Methyl hypofluorite, MeOF, easily made from MeOH and F2, proved to be an excellent source for the novel electrophilic methoxylium ion "MeO+". MeOF was reacted with the enol forms of carbonyls, producing in good to excellent yields the corresponding α-methoxy carbonyl derivatives. It was found that the methoxylation is best carried out on methyl enol ethers. Silyl enol ethers and enol acetates were also tested but with limited success. The reaction proceeds through an addition elimination mechanism.