114657-15-7

Upstream product

• 71831-21-5 4-(bromomethyl)benzyl alcohol 
• 589-29-7 p-xylylene glycol 
• 78757-46-7 α,α'-difluoro-p-xylene 
• 114657-13-5 1-Bromomethyl-4-phenylsulfanylmethyl-benzene 
• 623-24-5 1,4-bis(bromomethyl)benzene 

Downstream Products

• 1260369-13-8 4-{(4-Fluoromethylbenzyl)(4H-1,2,4-triazol-4-yl)amino}benzonitrile 

Relevant academic research and scientific papers

FLP-Catalyzed Monoselective C-F Functionalization in Polyfluorocarbons at Geminal or Distal Sites

We report frustrated Lewis pair (FLP)-catalyzed monoselective C-F activation in a range of aliphatic polyfluorocarbons with equivalent geminal and distal C-F positions. This methodology can be applied to aromatic-, ether-, thioether-, and alkyl-supported fluoromethyl groups. We expand the range of FLP base partners that work with monoselective C-F activation to include sulfide. The activated products can be subsequently functionalized via SN2 substitutions, photoredox-alkylations, and Suzuki couplings.

A Facile Method for the Fluorine Substitution of Phenylthio Group via Sulfonium Salts Using Cesium Fluoride

Monofluorinated compounds are easily prepared in good yields by treating phenyl sulfides with methyl fluorosulfonate and cesium fluoride in refluxing dichloromethane, successively.This reaction proceeds under so mild conditions as not to affect the coexisting bromine substituent.

Nucleophilic Substitution of Aliphatic Fluorides via Pseudohalide Intermediates

A method for aliphatic fluoride functionalization with a variety of nucleophiles has been reported. Carbon–fluoride bond cleavage is thermodynamically driven by the use of silylated pseudohalides TMS-OMs or TMS-NTf2, resulting in the formation of TMS-F and a trapped aliphatic pseudohalide intermediate. The rate of fluoride/pseudohalide exchange and the stability of this intermediate are such that little rearrangement is observed for terminal fluoride positions in linear aliphatic fluorides. The ability to convert organofluoride positions into pseudohalide groups allows facile nucleophilic attack by a wide range of nucleophiles. The late introduction of the nucleophiles also allows for a wide range of functional-group tolerance in the coupling partners. Selective alkyl fluoride mesylation is observed in the presence of other alkyl halides, allowing for orthogonal synthetic strategies.

Highly efficient one-pot labeling of new phosphonium cations with fluorine-18 as potential PET agents for myocardial perfusion imaging

Lipophilic cations such as phosphonium salts can accumulate in mitochondria of heart in response to the negative inner-transmembrane potentials. Two phosphonium salts [18F]FMBTP and [18F]mFMBTP were prepared and evaluated as potential myocardial perfusion imaging (MPI) agents in this study. The cations were radiolabeled via a simplified one-pot method starting from [18F]fluoride and followed by physicochemical property tests, in vitro cellular uptake assay, ex vivo mouse biodistribution, and in vivo rat microPET imaging. The total radiosynthesis time was less than 60 min including HPLC purification. The [18F] labeled compounds were obtained in high radiolabeling yield (～50%) and good radiochemical purity (>99%). Both compounds were electropositive, and their log P values at pH 7.4 were 1.16 ± 0.003 (n = 3) and 1.05 ± 0.01 (n = 3), respectively. Both [18F]FMBTP and [18F]mFMBTP had high heart uptake (25.24 ± 2.97% ID/g and 31.02 ± 0.33% ID/g at 5 min postinjection (p.i.)) in mice with good retention (28.99 ± 3.54% ID/g and 26.82 ± 3.46% ID/g at 120 min p.i.). From the PET images in rats, the cations exhibited high myocardium uptake and fast clearance from liver and small intestine to give high-contrast images across all time points. These phosphonium cations were radiosynthesized via a highly efficient one-pot procedure for potential MPI offering high heart accumulation and rapid nontarget clearance.

LABELING COMPOUND FOR PET

A labeling compound of the present invention includes a structure represented by formula (1) wherein X1 is 11CH3, CH218F, CF218F, 18F, 76Br or 124/sup