701-71-3

Usage

Classification

Fluoroalcohol

Contains

Fluorine atom and hydroxyl group

Usage

Organic synthesis and medicinal chemistry

Building block

Creation of other chemical compounds

Potential

Chiral auxiliary in asymmetric synthesis

Presence

Stereocenter on the carbon atom adjacent to the hydroxyl group

Applications

Development of pharmaceuticals and bioactive molecules

Unique structure

Contributes to its reactivity and potential uses

Versatility

Potential uses in various industries and research fields

Upstream product

• 503-09-3 epifluorohydrine 
• 591-51-5 phenyllithium 
• 1524-06-7 1-fluoro-3-phenylpropan-2-one 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 110270-43-4 (S)-α-(fluoromethyl)benzeneethanol 
• 336783-88-1 1-fluoromethyl-2-phenylethyl methanesulfonate 

Relevant academic research and scientific papers

Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins

Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [18F](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [18F]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

Activation of pig liver esterase in organic media with organic polymers. Application to the enantioselective acylation of racemic functionalized secondary alcohols

Pig liver esterase (PLE) shows practically no activity in acylation of alcohols with vinylic esters in organic solvents. However, addition of methoxypoly(ethylene glycol) (MPEG), bovine serum albumin (BSA), TentaGelAmino resin (TGA), or aminomethyl polystyrene (AMPS) confers activity to PLE in acylation of alcohols with vinyl propionate in organic solvents of low water content. Polymer-activated PLE showed high enantioselectivities (E > 100) in the acylation of racemic 1-alkoxy-, 1-ethylsulfanyl-, and 1-fluoro-3-aryl-2-propanols as well as racemic 1-phenoxy-2-propanol and racemic 1-methoxy-2-phenoxy-2-propanol. The synthetic utility of polymer-activated PLE has been demonstrated by the gram-scale resolution of 1-methoxy-3-phenyl-2-propanol, 1-ethylsulfanyl-3-phenyl-2-propanol, 1-methoxy-3-p-methoxyphenyl-2-propanol, 1- fluoro-3-phenyl-2-propanol, and 1-methoxy-3-phenoxy-2-propanol. In PLE-catalyzed acylation of alcohols with vinyl propionate, acetaldehyde and propionic acids, both being detrimental to the enzyme, are formed as byproducts. In addition, the water content of the system, which is critical for the activity of pig liver esterase, is lowered because of a competing enzymatic hydrolysis of the acyl donor. The polymers TGA, BSA, and AMPS not only scavenge the aldehyde and the acid through imine formation and neutralization, respectively, but replenish at least in part also the water consumed in the competing hydrolysis of the acyl donor. A recovery of PLE together with the polymer was achieved without major loss of activity through their immobilization on a water-saturated polyaramide membrane, which occurs spontaneously in organic solvents.