120466-66-2

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(2-chlorophenyl)ethanol is used as a key intermediate in the synthesis of various drugs, contributing to the development of new medications and therapeutic agents. Its chiral nature allows for the production of enantiomerically pure compounds, which is essential for ensuring the desired biological activity and minimizing potential side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-1-(2-chlorophenyl)ethanol is utilized as a precursor for the synthesis of pesticides and other agrochemicals. Its incorporation into these products can enhance their effectiveness and selectivity, leading to improved crop protection and reduced environmental impact.
Used in Fine Chemicals Industry:
(R)-1-(2-chlorophenyl)ethanol is employed as a building block for the production of fine chemicals, which are high-purity chemicals used in various applications such as fragrances, dyes, and specialty chemicals. Its versatility and reactivity make it a valuable component in the synthesis of these high-value products.
Used in Organic Synthesis:
As a versatile organic compound, (R)-1-(2-chlorophenyl)ethanol is used as a precursor in the synthesis of other organic compounds. Its reactivity and functional groups enable the formation of a wide range of chemical products, expanding its applications across various industries.
Used in Medicinal Chemistry:
Due to its potential biological activity, (R)-1-(2-chlorophenyl)ethanol is utilized in medicinal chemistry for the development of new pharmaceutical agents. Its unique structure and properties can be leveraged to design and synthesize novel compounds with specific therapeutic effects, contributing to the advancement of medical treatments.

Upstream product

• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 2039-87-4 2-chlorostyrene 
• 13524-04-4 2'-chloro-sec-phenethyl alcohol 
• 544-97-8 dimethyl zinc(II) 
• 89-98-5 2-chloro-benzaldehyde 
• 108-05-4 vinyl acetate 
• 67-63-0 isopropyl alcohol 
• 1796-62-9 (+/-)-1-(2-chlorophenyl)ethyl acetate 
• 942625-95-8 1-(trimethylsiloxy)-1-o-chloro-phenylethene 
• 2184-85-2 2-(2-chloro-phenyl)-propanoic acid 
• 873-31-4 2-chlorophenylacetylene 
• 577-16-2 2-Methylacetophenone 
• 154377-49-8 (R)-1-(2-chlorophenyl)-1-(trichlorosilyl)ethane 
• 1239700-56-1 2-(1-(2-chlorophenyl)vinyl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane 

Downstream Products

• 959999-91-8 2-propen-1-yl 1-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylate 
• 929040-32-4 methyl 5-(5-bromo-1H-benzimidazol-1-yl)-3-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}thiophene-2-carboxylate 
• 1245927-55-2 C₂₁H₁₆BrClN₂O₃S 
• 929040-33-5 5-(5-bromo-1H-benzimidazol-1-yl)-3-({(1R)-1-[2-chlorophenyl]ethyl}oxy)thiophene-2-carboxamide 
• 1245927-56-3 C₂₀H₁₅BrClN₃O₂S 
• 131864-75-0 (S)-1-(ortho-chlorophenyl)ethyl (R)-α-methoxy-α-trifluoromethylphenylacetate 
• 1326723-09-4 (S)-1-(ortho-chlorophenyl)ethyl (S)-α-methoxy-α-trifluoromethylphenylacetate 
• 1438465-84-9 5-tert-butyl-2-[(R)-1-(2-chloro-phenyl)-ethyl]-7-(3,3-difluoro-pyrrolidin-1-yl)-2H-[1,2,3]triazolo[4,5-d]pyrimidine 
• 1433359-72-8 5-tert-Butyl-3-[(R)-1-(2-chloro-phenyl)-ethyl]-7-(3,3-difluoro-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine 
• 929040-00-6 methyl 3-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-nitro-2-thiophenecarboxylate 
• 1228690-20-7 [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-chloro-phenyl)-ethyl ester 
• 13524-04-4 (S)-1-(2'-chlorophenyl)ethanol 
• 1402465-77-3 (R)-1-(2-chlorophenyl)ethyl 4-bromo-1-methyl-1H-pyrazol-5-ylcarbamate 
• 1402466-04-9 methyl 2-((1r,4r)-4-(4-(5-(((R)-1-(2-chlorophenyl)ethoxy)carbonylamino)-1-methyl-1H-pyrazol-4-yl)phenyl)cyclohexyl)acetate 

Relevant academic research and scientific papers

Amino alcohol effects on the ruthenium(II)-catalysed asymmetric transfer hydrogenation of ketones in propan-2-ol

A ruthenium(II) complex generated in situ from [{RuCl2(η6-C6Me6)}2], (1S,2S)-2-methylamino-1,2-diphenylethanol and KOH serves as an efficient catalyst for asymmetric transfer hydrogenation of acetophe

Asymmetric reduction of ketones by the acetone powder of Geotrichum candidum

Reduction of ketones with a reductant, 2-alkanol, by the acetone powder of Geotrichum candidum affords the corresponding (S)-alcohols of excellent ee in high yield.

Pushing the limits: Cyclodextrin-based intensification of bioreductions

The asymmetric reduction of ketones is a frequently used synthesis route towards chiral alcohols. Amongst available chemo- and biocatalysts the latter stand out in terms of product enantiopurity. Their application is, however, restricted by low reaction output, often rooted in limited enzyme stability under operational conditions. Here, addition of 2-hydroxypropyl-β-cyclodextrin to bioreductions of o-chloroacetophenone enabled product concentrations of up to 29 % w/v at full conversion and 99.97 % e.e. The catalyst was an E. coli strain co-expressing NADH-dependent Candida tenuis xylose reductase and a yeast formate dehydrogenase for coenzyme recycling. Analysis of the lyophilized biocatalyst showed that E. coli cells were leaky with catalytic activity found as free-floating enzymes and associated with the biomass. The biocatalyst was stabilized and activated in the reaction mixture by 2-hydroxypropyl-β-cyclodextrin. Substitution of the wild-type xylose reductase by a D51A mutant further improved bioreductions. In previous optimization strategies, hexane was added as second phase to protect the labile catalyst from adverse effects of hydrophobic substrate and product. The addition of 2-hydroxypropyl-β-cyclodextrin (11 % w/v) instead of hexane (20 % v/v) increased the yield on biocatalyst 6.3-fold. A literature survey suggests that bioreduction enhancement by addition of cyclodextrins is not restricted to specific enzyme classes, catalyst forms or substrates.

B-Chlorodiiso-2-ethylapopinocampheylborane: An extremely efficient chiral reducing agent for the reduction of prochiral ketones of intermediate steric requirements

B-Chlorodiiso-2-ethylapopinocampheylborane, Eap2BCl, prepared from 2-ethylapopinene and chloroborane-methyl sulfide reduces prochiral ketones of intermediate steric requirements to the product alcohols in very high ee.

Chiral Ru complex immobilized on mesoporous materials by ionic liquids as heterogeneous catalysts for hydrogenation of aromatic ketones

Four kinds of mesoporous material-supported ionic liquid phase catalysts containing chiral Ru complex were synthesized using mesoporous MCM-41, MCM-48, SBA-15 and amorphous SiO2, respectively. The results of N2 sorption and XRD indicated the successful immobilization of chiral Ru complex inside the channels of the mesoporous materials. These immobilized catalysts were evaluated in the asymmetric hydrogenation of aromatic ketones and the reaction conditions were optimized. Comparable catalytic activities and enantioselectivities to those of nonimmobilized counterpart were obtained. Moreover, all the four catalysts were stable and could be easily recovered for reuse for at least four times without obvious decrease in conversions and ee values. Especially, the SiO2-based catalyst still preserved high activity and enantioselectivity in the fifth run. The comparison experiments indicated that the two kinds of ionic liquids in the heterogeneous catalyst were beneficial to the enhancement of the stability of active species.

Asymmetric reduction of ketones with a germinated plant

A germinated radish sprout was used as a novel type of biocatalyst for the asymmetric reduction of ketones. The reactions proceeded with high enantioselectivities (>99% ee). The biocatalyst is easily obtainable from commercially available vegetable seeds and is very easy to use.

Stereoselective Reduction of Prochiral Ketones, Using Aluminum Hydride Reagents Prepared from LiAlH4 and Chiral Diethanolamines

The asymmetric reduction of prochiral ketones to chiral secondary alcohols by LiAlH4, modified with optically active diethanolamines, was studied.Asymmetric inductions of up to 94percent were obtained with these reagents.The stereoselectivity of the reaction was found to depend both upon the temperature at which the reduction was performed and upon the conditions under which the chiral aluminum hydride reagent had been prepared.By changing the substituents at the carbon atom α to nitrogen in the chiral auxiliary, either the (R)- and (S)-enantiomer of the secondary alcohol could be obtained in excess.

Synthesis of a fluorous ligand and its application for asymmetric addition of dimethylzinc to aldehydes

A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using a fluorous solvent or a fluorous column.

Enantioselective transfer hydrogenation of ketones with planar chiral?ruthenocene-based phosphinooxazoline ligands

1,2-Disubstituted planar chiral ruthenocene-based phosphinooxazoline ligands (Rc-PHOX, 3 and 4) were synthesized easily and applied in the transfer hydrogenation of ketones to chiral alcohols using 2-propanol as a source of hydrogen with excellent enantio

Asymmetric transfer hydrogenation of aromatic ketones catalyzed by SBA-15 supported Ir(I) complex under mild conditions

A heterogeneous catalyst of Ir(I)-9-amino epi-cinchonine complex immobilized on the surface of mesoporous SBA-15 was firstly synthesized and used in the asymmetric transfer hydrogenation of aromatic ketones. Enhanced enantioselectivity compared with homog