459-51-8

Basic information

• Product Name: Benzene, 1-fluoro-4-(fluoromethyl)-
• CAS NO: 459-51-8
• Molecular Formula: C7H6F2
• Molecular Weight: 128.121
• Mol File: 459-51-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, 1-fluoro-4-(fluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-fluoro-4-(fluoromethyl)-(459-51-8)
• EPA Substance Registry System: Benzene, 1-fluoro-4-(fluoromethyl)-(459-51-8)

Safety Data

• Hazardous Substances Data: 459-51-8(Hazardous Substances Data)

Upstream product

• 1960404-19-6 1,3-dioxoisoindolin-2-yl 2-(4-fluorophenyl)acetate 
• 459-46-1 4-Fluorobenzyl bromide 
• 459-57-4 4-fluorobenzaldehyde 
• 352-32-9 p-fluorotoluene 
• 462-06-6 fluorobenzene 
• 420-03-1 fluoromethyl alcohol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 352-11-4 1-chloromethyl-4-fluorobenzene 

Downstream Products

• 2248-13-7 1-(but-3-en-1-yl)-4-fluorobenzene 
• 99138-88-2 N-(4-fluorobenzyl)-4-methyl-2-nitroaniline 

Relevant articles and documents

METHOD AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

We report a redox-neutral method for nucleophilic fluorination of N-hydroxyphthalimide esters using an Ir photocatalyst under visible light irradiation. The method provides access to a broad range of aliphatic fluorides, including primary, secondary, and tertiary benzylic fluorides as well as unactivated tertiary fluorides, that are typically inaccessible by nucleophilic fluorination due to competing elimination. In addition, we show that the decarboxylative fluorination conditions are readily adapted to radiofluorination with [18F]KF. We propose that the reactions proceed by two electron transfers between the Ir catalyst and redox-active ester substrate to afford a carbocation intermediate that undergoes subsequent trapping by fluoride. Examples of trapping with O- and C-centered nucleophiles and deoxyfluorination via N-hydroxyphthalimidoyl oxalates are also presented, suggesting that this approach may offer a general blueprint for affecting redox-neutral SN1 substitutions under mild conditions.

Solvent free nucleophilic introduction of fluorine with [bmim][F]

1-n-Butyl-3-methylimidazolium fluoride ([bmim][F]) proved very efficient fluorinated reagent for nucleophilic substitution over sulfonate esters and alkyl halides. Preparation of the ionic liquid as well as its use as the reagent has been performed to be the more eco-friendly as possible. No organic solvent is needed for the fluoride introduction, reaction times are reduced by using microwave as the heating source, and the ionic liquids carefully recycled. Furthermore, no special care has to be taken as the presence of water in [bmim][F] was not deleterious to the transformation yield.