656-60-0

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-2-FLUOROCYCLOHEXANOL is utilized as an intermediate in the synthesis of various pharmaceuticals and biologically active compounds. Its unique structure contributes to the development of new medications, enhancing their efficacy and selectivity.
Used in Organic Synthesis:
As a solvent in organic synthesis, TRANS-2-FLUOROCYCLOHEXANOL plays a crucial role in facilitating chemical reactions, enabling the production of a wide range of organic compounds.
Used in Fragrance Industry:
TRANS-2-FLUOROCYCLOHEXANOL is employed in the manufacturing of fragrances, where its slightly sweet odor contributes to the creation of various scent profiles for different applications.
Used as a Chiral Building Block:
In the chemical industry, TRANS-2-FLUOROCYCLOHEXANOL serves as a chiral building block, providing a foundation for the development of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical processes.

InChI:InChI=1/C6H11FO/c7-5-3-1-2-4-6(5)8/h5-6,8H,1-4H2

Upstream product

• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 110-83-8 cyclohexene 
• 108-94-1 cyclohexanone 
• 694-82-6 2-fluorocyclohexanone 
• 14365-32-3 trans-2-fluorocyclohexanol 
• 930-68-7 cyclohexenone 
• 14365-32-3 trans-2-fluoro-cyclohexanol 
• 1561-86-0 2-chlorocyclohexanol 

Downstream Products

• 694-82-6 2-fluorocyclohexanone 
• 131508-81-1 C₁₃H₂₂F₂O₂ 
• 1381757-76-1 C₁₆H₂₃FN₄O₃ 
• 1259476-02-2 C₁₀H₁₅FO₃ 
• 1259475-98-3 C₁₄H₂₅FO₃Si 
• 114156-17-1 (E)-2-fluorocyclohexanone (S)-(-)-(1-methoxy-3-phenylprop-2-yl)imine 
• 114156-17-1 (Z)-2-fluorocyclohexanone (S)-(-)-(1-methoxy-3-phenylprop-2-yl)imine 
• 114156-22-8 2-benzyl-2-fluorocyclohexan-1-one 
• 114156-10-4 2-fluorocyclohexanone cyclohexylimine 
• 114156-21-7 2-fluoro-2-butylcyclohexanone 
• 15344-32-8 2-fluoro-2-methylcyclohexanone 
• 108-94-1 cyclohexanone 
• 65267-06-3 trans-2-fluoro-1-methoxycyclohexane 

Relevant academic research and scientific papers

Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins

A simple, user-friendly, metal-free protocol for the regioselective anti-Markovnikov hydrofluorination of olefins using readily available and inexpensive reagents has been developed. This new approach displays a broader scope than previously reported methodologies and has been applied to the late-stage fluorination of a complex molecule, giving rise to a fluorosteroid derivative. The stereochemistry of the process has also been studied in some detail.

Influence of Alcohol β-Fluorination on Hydrogen-Bond Acidity of Conformationally Flexible Substrates

Rational modulations of molecular interactions are of significant importance in compound properties optimization. We have previously shown that fluorination of conformationally rigid cyclohexanols leads to attenuation of their hydrogen-bond (H-bond) donat

Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation.

Fluorinated ε-caprolactone: Synthesis and ring-opening polymerization of new α-fluoro-ε-caprolactone monomer

Fluorinated polyester was synthesized from a novel α-fluoro-ε- caprolactone monomer (α-FCL). The monomer was synthesized from commercially available cyclohexene oxide in three steps. Baeyer-Villiger reaction using 3-chloroperoxybenzoic acid of the corresp

Conformational analysis of cis-2-halocyclohexanols; Solvent effects by NMR and theoretical calculations

Conformational problems often involve very small energy differences, even low as 0.5 kcal mol-1. This accuracy can be achieved by theoretical methods in the gas phase with the appropriate accounting of electron correlation. The solution behavio

Trifluoromethylthiocopper catalyzed oxirane ring opening

Trifluoromethylthiocopper has been found to catalyze the opening of the epoxide ring and to furnish not-so-easily accessible novel trifluoromethylthiolated α-hydroxy compounds. This communication presents the mechanism of the formation of the various comp

Regioselective synthesis of fluorohydrines via SN2-type ring-opening of epoxides with TBABF-KHF2

We found that the ring-opening fluorination of terminal epoxides using TBABF-KHF2 proceeds with high selectivity through the SN2 mechanism. As TBABF-KHF2 is easily obtainable, is stable, and can be used in glassware, it ca

Axial/equatorial proportions for 2-substituted cyclohexanones

Axial-equatorial conformational proportions have been measured for 2- substituted cyclohexanones in chloroform by the Eliel method for F, Cl, Br, I, MeO, MeS, Me2N, MeSe, and Me. For the first seven of these, at least five experimentally independent measurables were used and the resulting conformational preferences appear to be accurate to within 10%. Systematic errors degraded the results for MeSe and Me. For Me2N, the conformational preference also was measured for the first time at slow exchange in the low- temperature 13C spectrum in several solvents. In chloroform, steric and polar effects contribute to the conformational preferences, with steric effects dominant for large groups such as I and MeS.

Hypofluorous acid and acetonitrile: the taming of a reagent

The strong oxidant produced by the reaction of elemental fluorine with acetonitrile containing ca. 10percent water has been shown to be hypofluorous acid, HOF, which is stabilized by complexing to the solvent.The reaction represents a new and convenient method of preparing and handling HOF, a unique oxygenating reagent.The presence of acetonitrile results in subtle but significant changes in the chemical behavior of the HOF.Vibrational and NMR spectroscopic studies of the solutions resulting from this reaction, as well as of solutions prepared by dissolving neat HOF in dry acetonitrile, have shown that the complex as a 1:1 hydrogen-bridged entity, in which the HOF proton is most likely bonded to the nitrogen atom of the nitrile.The 19F NMR data indicate that the complexation reaction has an equilibrium constant of ca. 3 at room temperature, and that the enthalpy of formation of the complex is -14.3+/-0.5 kJ mol-1.The success of this method of synthesizing hypofluorous acid is a consequence of the very slow reaction between HOF and low concentrations of water in acetonitrile.This reaction accelarates drastically as the water content increases.As the solution composition approaches 100percent water, the rate constant appears to approach a limit of about 0.7 s-1 at 25 deg C, which may be the actual rate of reaction of HOF with the water.

Synthesis, Regioselective Deprotonation, and Stereoselective Alkylation of Fluoro Ketimines

Fluoroacetone imines of cyclohexylamine, valinol O-methyl ether, and phenylalaninol O-methyl ether and 2-fluorocyclohexanone imines of cyclohexylamine and phenylalaninol O-methyl ether were prepared.The temperature-dependent, regioselective deprotonation of these imines was employed in highly regioselective alkylation reactions.The deprotonation of fluoroacetone cyclohexylimine on the carbon bearing fluorine yielded only a single stereoisomer as determined by low temperature 19F NMR.In contrast, deprotonation of fluoroacetone O-benzyloximes was not regiospecific under any of the conditions examined.