120924-81-4

Basic information

• Product Name: (S)-1-(p-biphenyl)ethanol
• CAS NO: 120924-81-4
• Molecular Weight: 198.265
• Mol File: 120924-81-4.mol
• Article Data: 75

Chemical Properties

• Melting Point: 42.5-43.5 °C
• Boiling Point: 340.4±21.0 °C(Predicted)
• Density: 1.067±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-1-(p-biphenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(p-biphenyl)ethanol(120924-81-4)
• EPA Substance Registry System: (S)-1-(p-biphenyl)ethanol(120924-81-4)

Safety Data

• Hazardous Substances Data: 120924-81-4(Hazardous Substances Data)

Usage

General Description

(S)-1-(p-biphenyl)ethanol is a chemical compound with the molecular formula C14H14O. It is a chiral compound with two enantiomers, (R)- and (S)-1-(p-biphenyl)ethanol. (S)-1-(p-biphenyl)ethanol is used in various medicinal and industrial applications, particularly as a chiral building block in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential anti-inflammatory and antimicrobial properties. (S)-1-(p-biphenyl)ethanol is a colorless to pale yellow liquid at room temperature and is soluble in organic solvents such as ethanol and acetone.

Upstream product

• 2350-89-2 p-vinylbiphenyl 
• 99-91-2 para-chloroacetophenone 
• 98-80-6 phenylboronic acid 
• 1070704-01-6 2-(1-([1,1'-biphenyl]-4-yl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1591-31-7 4-iodo-biphenyl 
• 99-90-1 para-bromoacetophenone 
• 13329-40-3 4-Iodoacetophenone 
• 3562-73-0 1-(4-phenyl-phenyl)-1-ethanol 
• 5707-44-8 4-ethylbiphenyl 
• 108-05-4 vinyl acetate 
• 104013-25-4 S-p-iodo-α-methylbenzyl alcohol 
• 108-86-1 bromobenzene 
• 1173922-36-5 (S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol 
• 544-97-8 dimethyl zinc(II) 

Relevant articles and documents

An integrated immobilization strategy manipulates dual active centers to boost enantioselective tandem reactions

Manipulation of dual active centers via an integrated immobilization strategy can overcome the restriction of homogeneous catalysis in a sequential organic transformation. Herein, by utilizing hollow-shell-structured silica, hydrogen-bonding immobilization via a ship-in-a-bottle synthesis locks a Pd(carbene) center in a nanocage and covalent-bonding immobilization tethers chiral Ru(diamine) centers within the nanochannels, constructing a hetero-bifunctional catalyst. The benefit of this dual center manipulation enables a challenging Suzuki coupling-asymmetric transfer hydrogenation tandem reaction, and the advantage of this process provides various chiral biarylols with enhanced reactivity and enantioselectivity.

Borohydride intermediates pave the way for magnesium-catalysed enantioselective ketone reduction

A magnesium precatalyst for the highly enantioselective hydro-boration of CO bonds is reported. The mechanistic basis of the unprecedented selectivity of this transformation has been investi-gated experimentally by isolation of catalytic intermediates and theoretically by DFT calculations. The facile formation of a magnesium borohydride species is critical in overcoming competing pathways in the selectivity-determining insertion step.

Facile assembly of bifunctional, magnetically retrievable mesoporous silica for enantioselective cascade reactions

An integrated immobilization to encapsulate the Pd/C-coated magnetic nanoparticles within the chiral Ru/diamine-functionalized silica shell for the construction of a bifunctional magnetic catalyst is developed. This catalyst realizes a synergistic Suzuki cross-coupling/asymmetric transfer hydrogenation and a successive reduction/asymmetric transfer hydrogenation for the preparation of chiral aromatic alcohols.

Novel Insights into the Combination of Metal- and Biocatalysis: Cascade One-Pot Synthesis of Enantiomerically Pure Biaryl Alcohols in Deep Eutectic Solvents

One of the pioneering examples of chemoenzymatic cascades in water such as the palladium-catalysed Suzuki-cross coupling followed by an enzymatic reduction has been revisited by the employment of a medium containing Deep Eutectic Solvents (DESs) for the catalytic performance. Thus, the unique properties of these neoteric solvents enabled to reach high substrate concentration for the overall process. Moreover, both isolated enzymes and whole cells exhibited excellent activities which allowed to obtain a set of chiral biaryl alcohols in good yields and very high enantiomeric excess (>99 %).

Multiple Functionalized Hyperbranched Polyethoxysiloxane Promotes Suzuki Coupling Asymmetric Transfer Hydrogenation One-Pot Enantioselective Organic Transformations

Utilization of amphiphilic poly(ethylene glycol) monomethyl ether modified hyperbranched polyethoxysiloxane as a support for the construction of bifunctional heterogeneous catalysts enables a highly efficient catalytic system thanks to its amphiphilic nature in aqueous organic transformations. Herein, through a three-component self-assembly procedure, we incorporate palladium/phosphine and chiral ruthenium/diamine functionality within poly(ethylene glycol) monomethyl ether modified hyperbranched polyethoxysiloxane, fabricating a multiple functionalized polyethoxysiloxane based mesoporous material. Structural analyses and characterizations disclose that well-defined dual single-site active centers are distributed uniformly within monodisperse mesoporous silica nanoparticles. As a bifunctional heterogeneous catalyst, this material performs the one-pot enantioselective tandem reaction of Pd-catalyzed Suzuki cross-coupling and Ru-catalyzed asymmetric transfer hydrogenation, affording various chiral biaryl alcohols with high yields and up to 99 % enantioselectivity. Furthermore, the catalyst can be recovered and recycled eight times without loss of its catalytic activity, demonstrating the practicability of the preparation of optically pure biaryl alcohols in one-pot organic transformation.

Integrated Suzuki Cross-Coupling/Reduction Cascade Reaction of meta-/para-Chloroacetophenones and Arylboronic Acids under Batch and Continuous Flow Conditions

Overcoming the incompatibility of a pair of conflicting catalysts via a flow methodology has great significance in the practical applications for multistep organic transformations. In this study, a multiple continuous-flow system is developed, which can boost the reactivity and selectivity in a sequential enantioselective cascade reaction. During this process, a periodic mesoporous organosilica-supported Pd/carbene species as a Suzuki cross-coupling catalyst is packed in the first column reactor, whereas another periodic mesoporous organosilica-supported Ru/diamine species as an asymmetric transfer hydrogenation catalyst is packed in the second column reactor. As we envisioned, the initially Pd-catalyzed cross-coupling reaction of meta-/para-chloroacetophenones and aryl boronic acids followed by the subsequentially Ru-catalyzed reduction provides chiral biarylols with enhanced yields and enantioselectivities. Furthermore, the advantages of the easy handling and the simple procedure make this system an attractive application in a scale-up preparation of optically pure organic molecules under environmentally-friendly conditions.

Modular chemoenzymatic one-pot syntheses in aqueous media: Combination of a palladium-catalyzed cross-coupling with an asymmetric biotransformation

(Chemical Equation Presented) Two breeds of cat: A palladium-catalyzed Suzuki cross-coupling and an enzymatic reduction with an alcohol dehydrogenase from Rhodococcus sp. together enable the efficient and highly enantioselective synthesis of chiral biaryl alcohols in a one-pot process (see scheme).

Polydopamine-Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

Aqueous heterogeneous catalysis is a green, sustainable catalytic process that attracts increasing attention, but it often suffers from poor mass transfer, substrate adsorption and catalyst dispersion. Herein, we synthesized a type of amphiphilic core-shell catalysts with a hydrophilic polydopamine (PDA) shell and a hydrophobic dendritic organosilica nanoparticle (DON) core for heterogeneous catalysis in water. The hydrophilic shell allowed the catalyst dispersing well in water, and the hydrophobic core facilitated the absorption of organic reactants. The hierarchical core-shell structure facilitated rational arrangement of the location of catalytic species to match the reaction sequence. The obtained metal, enzyme and metal-enzyme amphiphilic catalysts demonstrated improved stability, selectivity and activity in aqueous reactions, including Pd-catalyzed cross-couplings (Suzuki, Liebeskind-Srogl, Heck and Sonogashira), enzymatic enantioselective reduction, chemoenzymatic cascade synthesis of chiral compounds and chemoenzymatic cascade degradation of organophosphates. The amphiphilic catalysts could be easily in situ recovered, and their high catalytic performance was sustained for five cycles.

Mn(i) phosphine-amino-phosphinites: a highly modular class of pincer complexes for enantioselective transfer hydrogenation of aryl-alkyl ketones

A series of Mn(i) catalysts with readily accessible and more π-accepting phosphine-amino-phosphinite (P′(O)N(H)P) pincer ligands have been explored for the asymmetric transfer hydrogenation of aryl-alkyl ketones which led to good to high enantioselectivities (up to 98%) compared to other reported Mn-based catalysts for such reactions. The easy tunability of the chiral backbone and the phosphine moieties makes P′(O)N(H)P an alternative ligand framework to the well-known PNP-type pincers.