14365-32-3

Basic information

• Product Name: Cyclohexanol, 2-fluoro-, (1R,2R)-rel-
• Synonyms: trans-2-fluorocyclohexanol
• CAS NO: 14365-32-3
• Molecular Formula: C6H11FO
• Molecular Weight: 118.151
• Mol File: 14365-32-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 69 - 71 °C (15 mmHg)
• CAS DataBase Reference: Cyclohexanol, 2-fluoro-, (1R,2R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 2-fluoro-, (1R,2R)-rel-(14365-32-3)
• EPA Substance Registry System: Cyclohexanol, 2-fluoro-, (1R,2R)-rel-(14365-32-3)

Safety Data

• Hazardous Substances Data: 14365-32-3(Hazardous Substances Data)

Upstream product

• 110-83-8 cyclohexene 
• 930-68-7 cyclohexenone 
• 108-94-1 cyclohexanone 
• 694-82-6 2-fluorocyclohexanone 
• 286-20-4 cyclohexane-1,2-epoxide 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 286-20-4 cyclohexene oxide 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 1561-86-0 2-chlorocyclohexanol 

Downstream Products

• 694-82-6 2-fluorocyclohexanone 
• 131508-81-1 C₁₃H₂₂F₂O₂ 
• 286-20-4 cyclohexane-1,2-epoxide 
• 126434-51-3 (1R,2R)-1-Fluoro-2-(2-fluoro-ethoxy)-cyclohexane 
• 65267-06-3 trans-2-fluoro-1-methoxycyclohexane 
• 433305-07-8 trans-1-acetoxy-2-fluorocyclohexane 
• 656-60-0 (±)-cis-2-fluorocyclohexanol 
• 51422-74-3 cis-1-Bromo-2-fluorocyclohexane 
• 1381757-76-1 C₁₆H₂₃FN₄O₃ 
• 1350744-37-4 carbonic acid 1-(5-{(R)-(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxy)propyl ester tans-2-fluoro-cyclohexyl ester 
• 1259476-02-2 C₁₀H₁₅FO₃ 
• 1259475-98-3 C₁₄H₂₅FO₃Si 
• 694-51-9 1-fluorocyclohexene 
• 462-06-6 fluorobenzene 

Relevant articles and documents

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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

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.

The Combination of Hydrogen Fluoride Salt and Aluminium Fluoride: an Efficient Solid Reagent for Epoxide Opening to give Fluorohydrins

The combination of hydrogen fluoride salt and porous aluminium fluoride (MHF2-AlF3) (M = alkali metal) is a stable and efficient solid reagent for promoting the ring-opening reaction of simple aliphatic oxiranes to give the fluorohydrins under sonication,

Synthesis of optically active vicinal fluorohydrins by lipase-catalyzed deracemization

Three microbial lipases have been used to deracemize trans-2-fluorocycloalkanols 2 both by hydrolysis of the corresponding acetates 3 or chloroacetates 4 and by esterification of the fluorohydrins 2 using vinyl acetate and vinyl chloroacetate, respectivel

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.

Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution

The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [ 18F]HF in a combination with (-)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-18F-fluorohydrines in 78-93% radiochemical yield (RCY) and 20-46% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [18F]F-MISO, which took 1.5 h and after solid phase-based purification delivered [ 18F]F-MISO in 81%/45% analytical/preparative RCY and 55% ee.