101325-12-6

Basic information

• Product Name: (R)-α-(4-tert-butylphenyl)ethanol
• Synonyms: (R)-α-(4-tert-butylphenyl)ethanol
• CAS NO: 101325-12-6
• Molecular Weight: 178.274
• Mol File: 101325-12-6.mol
• Article Data: 76

Chemical Properties

• CAS DataBase Reference: (R)-α-(4-tert-butylphenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-α-(4-tert-butylphenyl)ethanol(101325-12-6)
• EPA Substance Registry System: (R)-α-(4-tert-butylphenyl)ethanol(101325-12-6)

Safety Data

• Hazardous Substances Data: 101325-12-6(Hazardous Substances Data)

Usage

Description

(R)-α-(4-tert-butylphenyl)ethanol is a chiral alcohol compound, belonging to the phenylethanol family, with the chemical formula C14H22O. It is characterized by its colorless, viscous liquid state, a faint floral odor, and high stereospecificity due to its chiral nature. (R)-α-(4-tert-butylphenyl)ethanol is typically used in its enantiomerically pure form and can be synthesized through the reduction of the corresponding ketone or by the Grignard reaction followed by hydrolysis.

Uses

Used in Fragrance Industry:
(R)-α-(4-tert-butylphenyl)ethanol is used as a fragrance ingredient for its pleasant floral scent, adding value to various consumer products such as perfumes, colognes, and cosmetics.
Used in Pharmaceutical Industry:
(R)-α-(4-tert-butylphenyl)ethanol is used as a building block in the production of pharmaceuticals, contributing to the development of new medications and therapies.
Used in Flavor Industry:
This chiral alcohol is also utilized as a component in the creation of flavors for the food and beverage industry, enhancing the taste and aroma of various products.
Used in Organic Synthesis:
(R)-α-(4-tert-butylphenyl)ethanol serves as an important intermediate in the synthesis of other organic compounds, playing a crucial role in chemical research and development.

Upstream product

• 946615-31-2 C₁₂H₁₇Cl₃Si 
• 78-83-1 2-methyl-propan-1-ol 
• 943-27-1 4'-t-butylacetophenone 
• 71-23-8 propan-1-ol 
• 67-63-0 isopropyl alcohol 
• 13372-41-3 1-(tert-butyl)-4-(1-chloroethyl)benzene 
• 772-38-3 4-tert-Butylphenylacetylene 
• 1158482-86-0 (+)-(R)-1-(1-allyloxyethyl)-4-tert-butylbenzene 
• 101325-12-6 1-(4-tert-butylphenyl)ethanol 
• 936752-23-7 1-(4-tert-butylphenyl)vinyl diphenylphosphinate 
• 936752-31-7 1-(4-tert-butylphenyl)ethyl diphenylphosphinate 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 54519-07-2 vinyl ester of 3-phenylpropionic acid 

Downstream Products

• 119436-49-6 1-(1-bromoethyl)-4-(tert-butyl)benzene 
• 943-27-1 4'-t-butylacetophenone 
• 34386-42-0 (S)-1-(4-tert-butylphenyl)ethanol 
• 34386-42-0 (R)-1-(p-tert-butylphenyl)ethanol 
• 392727-87-6 1-(4-tert-butyl-2-nitrophenyl)ethyl acetate 
• 3282-56-2 4-tert-butylnitrobenzene 
• 866358-29-4 1-(1-bromovinyl)-4-(tert-butyl)benzene 
• 92975-15-0 2,3-di(tert-butylphenyl)-1,3-butadiene 
• 1203-16-3 <4-tert.-Butyl-α-methylbenzyl>-methyl-ether 
• 19494-36-1 1-tert-Butyl-4-(1-isopropoxy-ethyl)-benzene 
• 7364-19-4 4-ethyl-tert-butylbenzene 
• 81465-76-1 ethyl 5-(4-(tert-butyl)phenyl)isoxazole-3-carboxylate 

Relevant articles and documents

Ruthenium(II) pincer complexes with oxazoline arms for efficient transfer hydrogenation reactions

Well-defined PNNCN pincer ruthenium complexes bearing both strong phosphine and weak oxazoline donors were developed. These easily accessible complexes exhibit significantly better catalytic activity in transfer hydrogenation of ketones compared to their PN3P analogs. These reactions proceed under mild and base-free conditions via protonation- deprotonation of the 'NH' group in the aromatization-dearomatization process.

Catalytic asymmetric hydrogenation of aromatic ketones in room temperature ionic liquids

Polar bisphosphonic acid-derived Ru(BINAP)(DPEN)Cl2 precatalysts were synthesized and immobilized in room temperature ionic liquids (RTILs) for asymmetric hydrogenation of aromatic ketones with ee values of up to 98.7%. The performance of the Ru catalysts is highly dependent on the nature of imidazolium ILs. For the imidazolium ILs without acidic protons, both ILs and Ru catalysts were recycled by simple extraction and reused. Such a simple immobilization approach also prevented the leaching of Ru (and Ru catalysts) into the chiral secondary alcohol products, and should prove desirable for the production of pharmaceutical intermediates that are free from metal contaminants.

Practical Enantioselective Hydrogenation of Aromatic Ketones

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Magnetically recoverable chiral catalysts immobilized on magnetite nanoparticles for asymmetric hydrogenation of aromatic ketones

Novel heterogenized asymmetric catalysts were synthesized by immobilizing preformed Ru catalysts on magnetite nanoparticles via the phosphonate functionality and were characterized by a variety of techniques, including TEM, magnetization, and XRD. These nanoparticle-supported chiral catalysts were used for enantioselective heterogeneous asymmetric hydrogenation of aromatic ketones with very high enantiomeric excess values of up to 98.0%. The immobilized catalysts were easily recycled by magnetic decantation and reused for up to 14 times without loss of activity and enantioselectivity. Orthogonal nature of the present catalyst immobilization approach should allow the design of other superparamagnetic nanoparticle-supported asymmetric catalysts for a wide range of organic transformations. Copyright

Cyclodextrin-based systems for the stabilization of metallic(0) nanoparticles and their versatile applications in catalysis

In order to better respond to environmental standards, the development of metal nanoparticles using green approaches has exponentially grown for the last decade. Cyclodextrins, which are cyclic oligosaccharides composed of 6(α), 7(β) or 8(γ) glucopyranose units, have appeared to be interesting candidates for the synthesis of metal nanoparticles. Indeed, through the ability to form inclusion complexes or supramolecular adducts with organic molecules or metal precursors, cyclodextrins can be successfully employed to stabilize size-controlled zerovalent metallic nanoparticles active for hydrogenation reactions carried out in aqueous or gas-phase media. In this summary of our works, we report that cyclodextrins could be used in various forms and environments: (i) in free form, (ii) in complexed form with appropriate guests molecules, (iii) in combination with polymer matrices, (iv) in thermosensitive hydrogels and (v) immobilized onto porous carbons supports. All these studies highlight the fact that cyclodextrins can be seen as multi-task agents for nanocatalysis.

Efficient hydrogenation of carbonyl compounds using low-loaded supported copper nanoparticles under microwave irradiation

Highly active and dispersed copper (Cu) nanoparticles on mesoporous silicas have been prepared via microwave irradiation of a solution of copper precursors with a previously synthesized mesoporous hexagonal silica (HMS) support. The protocol allowed differently low-loaded (typically 0.5 wt%) Cu materials containing Cu metal and small quantities of metal oxides. Materials were then tested as catalysts in the hydrogenation of carbonyl compounds under microwave irradiation. Cu materials were found to be highly active, selective and reusable in the reduction of substituted aromatic ketones and aldehydes, providing quantitative conversion of starting material within 5-10 min reaction at mild reaction conditions with complete selectivity to the alcohols.

Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator

Electro-oxidative kinetic resolution of sec-alcohols mediated with a catalytic amount of an optically active N-oxyl was performed by use of a simple undivided cell under constant current conditions. The selectivity factor (S-value) increased remarkably when the reaction was performed at lower temperatures. The optically active N-oxyl was recovered and used repeatedly without any change in efficiency and selectivity. (C) 2000 Elsevier Science Ltd.

Ruthenium-Catalyzed Selective Hydrogenation of Epoxides to Secondary Alcohols

A ruthenium(II)-catalyzed highly selective Markovnikov hydrogenation of terminal epoxides to secondary alcohols is reported. Diverse substitutions on the aryl ring of styrene oxides are tolerated. Benzylic, glycidyl, and aliphatic epoxides as well as diepoxides also underwent facile hydrogenation to provide secondary alcohols with exclusive selectivity. Metal-ligand cooperation-mediated ruthenium trans-dihydride formation and its reaction involving oxygen and the less substituted terminal carbon of the epoxide is envisaged for the origin of the observed selectivity.

Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols which are important synthetic intermediates and end products for many industries. Driven by visible light only, this method is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. The combination of a heterogeneous dehydrogenation photocatalyst and a chiral molecular hydrogenation catalyst is essential to ensure two distinct pathways for the forward and reverse reactions. These reactions convert a large number of racemic aryl alkyl alcohols into their enantiomerically enriched forms in good yields and enantioselectivities.

Direct Asymmetric Hydrogenation and Dynamic Kinetic Resolution of Aryl Ketones Catalyzed by an Iridium-NHC Exhibiting High Enantio- and Diastereoselectivity

A chiral iridium carbene-oxazoline catalyst is reported that is able to directly and efficiently hydrogenate a wide variety of ketones in excellent yields and good enantioselectivity (up to 93 % ee). Moreover, when using racemic α-substituted ketones, excellent diastereoselectivities were obtained (dr 99:1) by dynamic kinetic resolution of the in situ formed enolate. Overall, the herein described hydrogenation occurs under ambient conditions using low hydrogen pressures, providing a direct and atom efficient method towards chiral secondary alcohols.