325-24-6

Usage

Structure

Naphthalene ring with a fluoroethoxy group attached to one of the carbon atoms

Type of compound

Organic compound

Fluorinated derivative

Yes (derived from naphthalene)

Common uses

Building block in the synthesis of pharmaceuticals and agrochemicals, chemical intermediate in the production of other organic compounds

Industrial applications

Research and industrial applications, particularly in the field of organic chemistry and chemical synthesis

Presence of fluoroethoxy group

Enhances compound's usefulness in various applications

InChI:InChI=1/C12H11FO/c13-7-8-14-12-6-5-10-3-1-2-4-11(10)9-12/h1-6,9H,7-8H2

Upstream product

• 762-49-2 2-fluoroethyl bromide 
• 135-19-3 β-naphthol 
• 875-83-2 sodium 2-naphtholate 
• 1207991-05-6 2-fluoroethyl 4-tert-butyl-2,6-dimethylbenzenesulfonate 
• 383-51-7 2-fluoroethyl benzenesulfonate 
• 63649-88-7 2-(naphthalene-2-yloxy)ethyl methanesulfonate 

Relevant academic research and scientific papers

Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity

Versatile, safe, shelf-stable, and easy-to-handle fluorinating agents are strongly desired in both academic and industrial arenas, since fluorinated compounds have attracted considerable interest in many areas, such as drug discovery, due to the unique effects of fluorine atoms when incorporated into molecules. This article describes the synthesis, properties, and reactivity of many substituted and thermally stable phenylsulfur trifluorides, in particular, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead, 1k), as a crystalline solid having surprisingly high stability on contact with water and superior utility as a deoxofluorinating agent compared to current reagents, such as DAST and its analogues. The roles of substiuents on 1k in thermal and hydrolytic stability, fluorination reactivity, and the high-yield fluorination mechanism it undergoes have been clarified. In addition to fluorinations of alcohols, aldehydes, and enolizable ketones, 1k smoothly converts non-enolizable carbonyls to CF2 groups, and carboxylic groups to CF3 groups, in high yields. 1k also converts C(=S) and CH3SC(=S)O groups to CF2 and CF3O groups, respectively, in high yields. In addition, 1k effects highly stereoselective deoxofluoro-arylsulfinylation of diols and amino alcohols to give fluoroalkyl arylsulfinates and arylsulfinamides, with complete inversion of configuration at fluorine and the simultaneous, selective formation of one conformational isomer at the sulfoxide sulfur atom. Considering the unique and diverse properties, relative safety, and ease of handling of 1k in addition to its convenient synthesis, it is expected to find considerable use as a novel fluorinating agent in both academic and industrial arenas.

METHODS FOR PREPARING FLUOROALKYL ARYLSULFINYL COMPOUNDS AND FLUORINATED COMPOUNDS THERETO

Novel preparative methods for fluoroalkyl arylsulfinyl compounds are disclosed. Fluorinated compounds as useful fluorinated compounds, intermediates, or builing blocks are disclosed. Useful applications of the fluoroalkyl arylsulfinyl compounds are shown.

A new class of SN2 reactions catalyzed by protic solvents: Facile fluorination for isotopic labeling of diagnostic molecules

Aprotic solvents are usually preferred for the SN2 reactions, because nucleophilicity and hence SN2 reactivity are severely retarded by the influence of the partial positive charge of protic solvents. In this work, we introduce a remarkable effect of using tertiary alcohols as a reaction medium for nucleophilic fluorination with alkali metal fluorides. In this novel synthetic method, the nonpolar protic tert-alcohol enhances the nucleophilicity of the fluoride ion dramatically in the absence of any kind of catalyst, greatly increasing the rate of the nucleophilic fluorination and reducing formation of byproducts (such as alkenes, alcohols, or ethers) compared with conventional methods using dipolar aprotic solvents. The great efficacy of this method is a particular advantage in labeling radiopharmaceuticals with [18F]fluorine (t1/2 = 110 min) for positron emission tomographic (PET) imaging, and it is illustrated by the synthesis of four [ 18F]fluoride-radiolabeled molecular imaging probes-[ 18F]FDG, [18F]FLT, [18F]FP-CIT, and [ 18F]FMISO-in high yield and purity and in shorter times compared to conventional syntheses.

Pesticidal 2-fluoroethyl ethers

Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R1 R2m Ar(OCH2 CH2 F)n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and cla