34281-92-0

Basic information

• Product Name: (1S,2R)-(+)-TRANS-2-PHENYL-1-CYCLOHEXANOL
• Synonyms: (1S,2R)-2-PHENYL-1-CYCLOHEXANOL;(1S,2R)-(+)-TRANS-2-PHENYL-1-CYCLOHEXANOL;(1S,2R)-TRANS-2-PHENYL-1-CYCLOHEXANOL;(1R,2S)-(+)-TRANS-2-PHENYL-1-CYCLOHEXANOL;(1S,2R)-(+)-TRANS-2-PHENYL-1-CYCLOHEXANO L, 99% (98% EE/GLC);(1S,2R)-TRANS-2-PHENYL-1-CYCLOHEXANOL 99+%;(1S)-2β-Phenyl-cyclohexane-1α-ol;(1S)-2β-Phenylcyclohexane-1α-ol
• CAS NO: 34281-92-0
• Molecular Formula: C₁₂H₁₆O
• Molecular Weight: 176.25
• EINECS: 219-111-2
• Product Categories: chiral;Asymmetric Synthesis;Synthetic Organic Chemistry;Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 34281-92-0.mol
• Article Data: 74

Chemical Properties

• Melting Point: 64-66 °C(lit.)
• Boiling Point: 276-281 °C(lit.)
• Flash Point: 113.326 °C
• Appearance: white to light yellow crystal powde
• Density: 0.9452 (rough estimate)
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 60 ° (C=10, MeOH)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Methanol
• BRN: 4669439
• CAS DataBase Reference: (1S,2R)-(+)-TRANS-2-PHENYL-1-CYCLOHEXANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-(+)-TRANS-2-PHENYL-1-CYCLOHEXANOL(34281-92-0)
• EPA Substance Registry System: (1S,2R)-(+)-TRANS-2-PHENYL-1-CYCLOHEXANOL(34281-92-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 34281-92-0(Hazardous Substances Data)

Usage

Description

(1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol is a white to light yellow crystalline powder with specific stereochemistry, characterized by its (1S,2R) configuration and (+) optical rotation. It is a cyclohexanol derivative featuring a phenyl group attached to the cyclohexane ring in a trans configuration.

Uses

Used in Pharmaceutical Research:
(1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol is used as a substrate for studying the permeability of alcohol enantiomers through imprinted membranes. This application is crucial in determining the permeability coefficient, which is an essential parameter in the development of drug delivery systems and understanding the behavior of chiral molecules in biological systems.
Used in Chemical Synthesis:
(1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol can be utilized as a chiral building block or intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique stereochemistry makes it a valuable component in creating enantiomerically pure compounds with specific biological activities.
Used in Analytical Chemistry:
(1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol can also be employed as a reference material or standard in analytical chemistry for the calibration of instruments and methods used in the separation and quantification of enantiomers, such as chiral chromatography and circular dichroism spectroscopy.
Used in Material Science:
The specific stereochemistry and chemical structure of (1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol may also find applications in the development of novel materials with tailored properties, such as chiral catalysts, sensors, or polymers with specific interactions and functions.

InChI:InChI=1/C12H16O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-3,6-7,11-13H,4-5,8-9H2/t11-,12+/m1/s1

Upstream product

• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 90-43-7 2-Phenylphenol 
• 771-98-2 1-Phenylcyclohexene 
• 36367-76-7 cis-2-Phenylcyclohexyl-p-bromobenzene sulfonate 
• 36367-76-7 trans-2-Phenylcyclohexyl-p-bromobenzene sulphonate 
• 4829-01-0 (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide 
• 2362-61-0 trans-2-Phenylcyclohexanol 
• 462636-88-0 4,4,5,5-tetramethyl-2-(3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)-1,3,2-dioxaborolane 
• 1444-64-0 2-phenylcyclohexanol 
• 822-87-7 2-Chlorocyclohexanone 
• 108-86-1 bromobenzene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 100-58-3 phenylmagnesium bromide 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 5434-83-3 optically inactive boric acid tris-(cis-2-phenyl-cyclohexyl ester) 
• 94310-98-2 (+/-)-phenylcarbamic acid-(cis-2-phenyl-cyclohexyl ester) 
• 22040-54-6 cis-2-phenyl-cyclohexyl acetate 
• 102003-69-0 cis-2-Hydroxy-3-<2-phenyl-cyclohexyloxy>-propylchlorid 
• 134311-26-5 (+)-(1S,2R)-trans-2-phenylcyclohexyl (S)-p-toluenesulfinate 
• 134357-69-0 (+)-(1S,2R)-trans-2-phenylcyclohexyl (R)-p-toluenesulfinate 
• 134357-71-4 (+)-(1S,2R)-trans-2-phenylcyclohexyl (R)-methanesulfinate 
• 134311-28-7 (+)-(1S,2R)-trans-2-phenylcyclohexyl (S)-methanesulfinate 
• 134311-29-8 (+)-(1S,2R)-trans-2-phenylcyclohexyl 2-propanesulfinate 
• 109334-05-6 1-Methyl-4-[1-((1S,2R)-2-phenyl-cyclohexyloxymethyl)-vinyl]-benzene 
• 134311-27-6 (+)-trans-2-phenylcyclohexyl 2-naphthalenesulfinate 
• 129966-10-5 (S)-trans-2-phenylcyclohexyl carbamate 
• 72331-10-3 cis-1,2,3,4,4a,10b-hexahydro-4H-dibenzopyran-6-one 
• 771-98-2 1-Phenylcyclohexene 

Relevant articles and documents

Hydroboration. 80. Preparation of (trans-2-Phenylcyclopentyl)- and (trans-2-Phenylcyclohexyl)boronates of Very High Enantiomeric Purities

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Synthesis method of chiral trans-2-substituted naphthenic alcohol

The invention relates to a synthesis method of chiral trans-2-substituted naphthenic alcohol. The invention provides a method for synthesizing chiral trans-cycloalkanol through asymmetric hydrogenation of palladium-catalyzed 2-substituted cyclic ketone. According to the method,a chiral diphosphine P-P * complex of metal palladium is taken as a catalyst, an acid additive is used in cooperation, asymmetric hydrogenation is carried out on a 2-substituted cyclic ketone compound to obtain a corresponding chiral trans-cycloalkanol compound. the enantiomeric excess of the chiral trans-cycloalkanol compound can reach 97% at most, and the trans-selectivity of the chiral trans-cycloalkanol compound is up to 20: 1. The method is simple and convenient to operate, practical, easy to implement, high in yield, high in atom economy and environment-friendly; the catalyst is commercially available; the reaction conditions are mild; and the method has a potential practical application value.

Preparation method of (1S, 2R)-2-phenylcyclohexanol

The invention provides a preparation method of (1S, 2R)-2-phenylcyclohexanol. The preparation method specifically comprises the following steps: mixing and reacting a cyclohexene oxide solution, a tetrahydrofuran solution of phenyl magnesium bromide, and cuprous chloride or cuprous bromide for 1-3 h, and performing quenching treatment with an aqueous saturated ammonium chloride or saturated ammonium sulfate solution; and collecting the obtained upper organic layer, carrying out concentration, distillation and recrystallization treatment to obtain a raceme of chiral 2-phenylcyclohexanol, and carrying out resolution treatment on the raceme of chiral 2-phenylcyclohexanol to obtain (1S, 2R)-2-phenylcyclohexanol. The method allows the ee value of the obtained product to reach 98% or above, theprocess is simple, and the product purity is high.