20585-34-6

Basic information

• Product Name: (S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID
• Synonyms: (2S)-CYCLOHEXYL(HYDROXY)PHENYLACETIC ACID;(S)-(+)-α-Phenyl-cyclohexaneglycolic Acid;(αS)-α-Cyclohexyl-α-hydroxy-benzeneacetic Acid;(S)-2-Cyclohexyl-2-phenylglycolic acid;alpha-Cyclohexyl-L-mandelic acid;(S)-2,-Cyclohexylmandelic acid;(S-2-Cyclohexyl-2-Hydroxy-2-Phenylacetic Acid
• CAS NO: 20585-34-6
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.29
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 20585-34-6.mol
• Article Data: 37

Chemical Properties

• Melting Point: 143-145°C
• Boiling Point: 408.6°Cat760mmHg
• Flash Point: 215.1°C
• Appearance: /
• Density: 1.206g/cm³
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: -20°C Freezer
• PKA: 3.49±0.25(Predicted)
• CAS DataBase Reference: (S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID(20585-34-6)
• EPA Substance Registry System: (S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID(20585-34-6)

Safety Data

• Hazardous Substances Data: 20585-34-6(Hazardous Substances Data)

Usage

Description

(S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID, also known as (S)-2-Cyclohexyl-2-hydroxy-phenylacetic Acid (CAS# 20585-34-6), is a white to off-white solid compound with significant utility in the field of organic synthesis. Its unique molecular structure endows it with versatile chemical properties, making it a valuable component in the development of various chemical products and pharmaceuticals.

Uses

Used in Organic Synthesis:
(S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID is used as a key intermediate in the synthesis of complex organic molecules. Its unique structure allows for the creation of a wide range of compounds with diverse applications in various industries.
Used in Pharmaceutical Industry:
(S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID is used as a building block for the development of new pharmaceuticals. Its chemical properties make it a promising candidate for the creation of novel drugs with potential therapeutic benefits.
Used in Chemical Research:
(S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID is utilized as a research compound in the study of various chemical reactions and processes. Its unique properties provide valuable insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Material Science:
(S)-CYCLOHEXYL-HYDROXY-PHENYL-ACETIC ACID is employed in the development of new materials with specific properties. Its incorporation into various formulations can lead to the creation of materials with enhanced characteristics, such as improved strength, durability, or chemical resistance.

InChI:InChI=1/C14H18O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-8,12,17H,2,5-6,9-10H2,(H,15,16)/t14-/m1/s1

Upstream product

• 31197-69-0 ethyl 2-cyclohexyl-2-hydroxy-2-phenylacetate 
• 76-93-7 Benzilic acid 
• 5633-20-5 oxybutynin 
• 931-50-0 cyclohexylmagnesium bromide 
• 67-56-1 methanol 
• 424792-59-6 methyl 2-(2'-cyclohexen-1'-yl)-2-hydroxy-2-phenylacetate 
• 151900-28-6 methanol hydrate 
• 1508-65-2 Oxybutynin chloride 
• 20585-33-5 S-(+)-phenyl-2 cyclohexyl-2 hydroxy-2 acetate de methyle 
• 91704-75-5 (S)-(-)-1-cyclohexyl-1-phenyl-1,2-etanediol 
• 944324-90-7 (+/-)-[(1-cyano-1-cyclohexyl-1-phenylmethoxy)carbonyl]methyl acetate 
• 944324-96-3 (+/-)-1-cyano-1-cyclohexyl-1-phenylmethyl hydroxyacetate 
• 90581-52-5 cis-(2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one 
• 4335-77-7 cyclohexylmandelic acid 

Downstream Products

• 93005-50-6 cyclohexylidene-phenyl-acetic acid 
• 6313-70-8 dicyclohexyl-hydroxy-acetic acid 
• 128887-53-6 Cyclohexyl-hydroxy-phenyl-acetic acid 3-pyrrolidin-1-yl-propyl ester 
• 128887-54-7 Cyclohexyl-hydroxy-phenyl-acetic acid 3-piperidin-1-yl-propyl ester 
• 128887-55-8 Cyclohexyl-hydroxy-phenyl-acetic acid 3-azepan-1-yl-propyl ester 
• 405089-66-9 2-Cyclohexyl-2-hydroxy-2-phenyl-1-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanone 
• 20585-39-1 (2R)-2-Cyclohexyl-2-hydroxy-2-phenylacetic acid 
• 201942-95-2 (-)-2-cyclohexyl-N-(4-dimethylamino-2-butynyl)-2-hydroxy-2-phenylacetamide 
• 10399-13-0 methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate 
• 25520-98-3 cyclohexyl-hydroxy-phenyl-acetic acid-(2-dimethylamino-ethyl ester) 
• 14657-85-3 Cyclohexyl-phenyl-glykolsaeure-<2-brom-aethylester> 
• 3570-96-5 demethyloxyphenonium 
• 96167-82-7 cyclohexyl-hydroxy-phenyl-acetic acid-(2-piperidino-ethyl ester) 
• 712356-35-9 (1α, 5α, 6α)-6-N-(3-azabicyclo [3.1.0] cyclohexyl)-2-hydroxy-2-cyclohexyl-2-phenyl acetamide 

Relevant articles and documents

Equilibrium studies on reactive extraction of α-cyclohexylmandelic enantiomers using hydrophilic β-Cyclodextrin derivatives extractants

β-Cyclodextrin (β-CD) is negligibly soluble in organic liquids and can be modified to achieve a higher solubility in water. In this paper, racemic α-cyclohexyl-mandelic acid (α-CHMA) was separated by chiral reactive extraction with aqueous β-cyclodextrin derivatives. Hydroxypropyl-β-cyclodextrin (HP-β-CD), hydroxyethyl-β- cyclodextrin (HE-β-CD), and methyl-β-cyclodextrin (Me-β-CD) were selected as chiral selectors for reactive extraction of α-CHMA enantiomers from organic phase to aqueous phase. Factors affecting the extraction efficiency were investigated, including the types of organic solvents and β-CD derivatives, the concentrations of the chiral selector and α-CHMA enantiomers, pH and temperature. The experimental results demonstrate that HP-β-CD, HE-β-CD, and Me-β-CD have stronger recognition abilities for S-α-CHMA than for R-α-CHMA. Among the three derivatives, HP-β-CD shows the strongest separation factor for α-CHMA enantiomers. A high enantioseparation efficiency with a maximum separation factor (α) of 2.02 is observed at pH 2.5 and 5 °C.

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

Nitrilases

The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition, methods of designing new nitrilases and methods of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.

Enantioseparation of mandelic acid and α-Cyclohexylmandelic acid using an alcohol/salt-based aqueous two-Phase system

An alcohol/salt-based aqueous two-phase system (ATPS) was employed for enantioseparation of (R,S)-mandelic acid (MA) and (R,S)-a-cyclohexylmandelic acid (a-CHMA). Sulfonated β-cyclodextrin (Sf-β-CD) with different degrees of substitution (DS) was consider