134356-70-0

Usage

Uses

Used in Pharmaceutical Research and Organic Synthesis:
(R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol is utilized as a chiral building block for the production of various pharmaceuticals and biologically active molecules, due to its unique structural features that facilitate the creation of enantiomerically pure compounds.
Used in Synthesis of Complex Molecules:
(R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol serves as a reagent in the synthesis of complex molecules, contributing to the development of advanced chemical entities with specific therapeutic or functional properties.
Used in Preparation of Chiral Ligands and Catalysts:
(R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol is employed as a starting material for the preparation of chiral ligands and catalysts, which are essential in asymmetric synthesis and other enantioselective processes, enhancing the efficiency and selectivity of chemical reactions.
Used in Antimicrobial and Antifungal Research:
In research studies, (R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol has demonstrated potential as an antimicrobial and antifungal agent, indicating its possible use in the development of new treatments for infectious diseases.
Used in Medicine, Chemistry, and Materials Science:
Given its versatility, (R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol finds applications across multiple disciplines, including medicine for drug development, chemistry for the synthesis of novel compounds, and materials science for the creation of new functional materials.

Upstream product

• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 876-27-7 4-chlorophenyl acetate 
• 61592-48-1 2-Chloro-1-(4-fluorophenyl)ethanol 
• 108-05-4 vinyl acetate 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 
• 332-43-4 1-(2-chloroethyl)-4-fluorobenzene 
• 108-22-5 Isopropenyl acetate 
• 1737-34-4 1-(chloroethynyl)-4-fluorobenzene 
• 134295-34-4 S-(+)-2-chloro-1-(4-fluorophenyl)ethanol acetate 
• 593-71-5 Chloroiodomethane 
• 459-57-4 4-fluorobenzaldehyde 
• 405-99-2 para-fluorostyrene 

Downstream Products

• 134295-34-4 S-(+)-2-chloro-1-(4-fluorophenyl)ethanol acetate 
• 126534-43-8 [R]-1-chloro-2-(4-fluorophenyl)-2-ethanol 
• 41823-14-7 1-(2-Chloro-1-fluoro-ethyl)-4-fluoro-benzene 
• 126534-42-7 (S)-1-chloro-2-hydroxy-2-(p-fluorophenyl)ethane 
• 18511-62-1 (2S)-2-(4-fluorophenyl)oxirane 
• 920796-73-2 (6S)-6-(4-fluorophenyl)-4-benzylmorpholine-3-one 
• 503860-57-9 UDA-680 
• 920796-74-3 (2S)-4-benzyl-2-(4-fluorophenyl)morpholine 
• 503860-58-0 (2S)-2-(4-fluorophenyl)morpholine hydrochloride 
• 920797-21-3 N-benzyl-2-chloro-N-[(2S)-2-(4-fluorophenyl)-2-hydroxyethyl]acetamide 
• 1185198-25-7 (R)-2-amino-1-(4-fluoro-phenyl)-ethanol hydrochloride 
• 1184850-40-5 (R)-2-(6-chloro-pyrimidin-4-ylamino)-1-(4-fluoro-phenyl)-ethanol 

Relevant academic research and scientific papers

Thiourea catalysis of NCS in the synthesis of chlorohydrins

Thiourea catalysis of reactions utilizing N-succinimides is demonstrated with NCS chlorination of olefins in the presence of water to afford chlorohydrins.

Unmasking the Hidden Carbonyl Group Using Gold(I) Catalysts and Alcohol Dehydrogenases: Design of a Thermodynamically-Driven Cascade toward Optically Active Halohydrins

A concurrent cascade combining the use of a gold(I) N-heterocyclic carbene (NHC) and an alcohol dehydrogenase (ADH) is disclosed for the synthesis of highly valuable enantiopure halohydrins in an aqueous medium and under mild reaction conditions. The meth

Biocatalytic preparation of a key intermediate of antifungal drugs using an alcohol dehydrogenase with high organic tolerance

In this study, an alcohol dehydrogenase derived from Lactobacillus kefir (LkADH) was engineered and a simple and practical bioreduction system was developed for the preparation of (R)-2-chloro-1-(2, 4-dichlorophenyl) ethanol ((R)-CDPO), a key intermediate for the synthesis of antifungal drugs. Through active pocket iterative saturation mutagenesis, mutant LkADH-D18 (Y190C/V196L/M206H/D150H) was obtained with high stereoselectivity (99% ee, R vs 87% ee, S) and increased activity (0.44 μmol·min?1·mg?1). LkADH-D18 demonstrated NAD(P)H regeneration capability using a high concentration of isopropanol (IPA) as a co-substrate. Using 40% IPA (v/v), 400 mM of (R)-CDPO (90.1 g·L-1) was obtained via complete substrate conversion using 40 mg·mL?1 LkADH-D18 wet cells. The biocatalytic process catalyzed at constant pH with the cheap co-solvent IPA contributed to improved isolated yield of (R)-CDPO (97%), lower reaction cost, and simpler downstream purification, indicating the potential utility of LkADH-D18 in future industrial applications.

Deep Eutectic Solvents as Media in Alcohol Dehydrogenase-Catalyzed Reductions of Halogenated Ketones

The application of deep eutectic solvents (DESs) in biotechnological processes has gained an outstanding relevance, as they can be used as greener media to obtain higher productivities and selectivities. In the present contribution, an eutectic mixture composed of choline chloride (ChCl): glycerol (1 : 2 mol/mol) has been used as a reaction medium in combination with Tris?SO4 50 mM buffer pH 7.5, applied to the alcohol dehydrogenase (ADH)-catalyzed reduction of various carbonyl precursors of chiral halohydrins. These alcohols are key intermediates of biologically active compounds, and hence they are of industrial interest. In the presence of up to 50 % v/v of DES, these biotransformations were achieved up to 300–400 mM of the α-halogenated ketone substrate, getting access to the final compounds with excellent conversions (usually >90 %) and enantiomeric excess (ee >99 %). Among the different ADHs tested, two stereocomplementary enzymes (Lactobacillus brevis ADH and Rhodococcus ruber ADH) afforded the best results, so both alcohol enantiomers could be obtained in all the studied examples. Selected bioreductions were scaled up to 250 mg and 1 g, demonstrating the potential that DESs can offer as media in redox processes for substrates with low solubility in water.

Stereoselective synthesis of the key intermediate of ticagrelor and its diverse analogs using a new alcohol dehydrogenase from Rhodococcus kyotonensis

Bioreduction catalyzed by alcohol dehydrogenase/reductase is one of the most valuable biotransformation processes widely used in industry. The (S)-2-Chloro-1-(3, 4-difluorophenyl) ethanol is a key chiral synthon for synthesizing the antithrombotic agent ticagrelor. Herein, a new alcohol dehydrogenase (named Rhky-ADH) identified from Rhodococcus kyotonensis by an enzyme promiscuity-based genome mining method was successfully cloned and functionally expressed in Escherichia coli. The whole cell biocatalyst harboring Rhky-ADH was biochemically characterized and was shown to be able to convert 2-Chloro-1-(3, 4-difluorophenyl) ethanone to (S)-2-Chloro-1-(3, 4-difluorophenyl) ethanol with more than 99 % enantiomeric excess (ee) and 99 % conversion. Our data showed that the optimum temperature and pH for Rhky-ADH were 25 °C and pH 8.0, respectively. The addition of NADH and an appropriate concentration of isopropanol enhanced the activity of Rhky-ADH, and 1 mM Mn2+ increased the enzyme activity by about 8 %. Substrate specificity experiments showed that Rhky-ADH had notable enzyme promiscuity and could reduce several ketones with high stereoselectivity. Our investigation on this novel enzyme adds another rare biocatalyst to the toolbox for producing chiral alcohols, which are widely used in the pharmaceutical industry.

Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: A case of study and rationalization

Racemic phenylethyl halohydrins acetates containing several groups attached to the aromatic ring were resolved via hydrolysis reaction in the presence of lipase B from Candida antarctica (Novozym 435). In all cases, the kinetic resolution was highly selective (E > 200) leading to the corresponding (S)-β-halohydrin with ee > 99 %. However, the time required for an ideal 50 % conversion ranged from 15 min for 2,4-dichlorophenyl chlorohydrin acetate to 216 h for 2-chlorophenyl bromohydrin acetate. Six chlorohydrins and five bromohydrins were evaluated, the latter being less reactive. For the β-brominated substrates, steric hindrance on the aromatic ring played a crucial role, which was not observed for the β-chlorinated derivatives. To shed light on the different reaction rates, docking studies were carried out with all the substrates using MD simulations. The computational data obtained for the β-brominated substrates, based on the parameters analysed such as NAC (near attack conformation), distance between Ser-O and carbonyl-C and oxyanion site stabilization were in agreement with the experimental results. On the other hand, the data obtained for β-chlorinated substrates suggested that physical aspects such as high hydrophobicity or induced change in the conformation of the enzymatic active site are more relevant aspects when compared to steric hindrance effects.

Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates

The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).

Cascade bio-hydroxylation and dehalogenation for one-pot enantioselective synthesis of optically active β-halohydrins from halohydrocarbons

A stereoselective hydroxylation and enantioselective dehalogenation cascade reaction was developed for the synthesis of optically active β-haloalcohols from halohydrocarbons. This cascade system employed P450 and halohydrin dehalogenase as two compatible biocatalysts, allowing a straightforward, greener and efficient access to β-halohydrins with excellent enantioselectivities (98-99%).

Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts

A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).

Iridium-Catalyzed Asymmetric Hydrogenation of Halogenated Ketones for the Efficient Construction of Chiral Halohydrins

Iridium-catalyzed asymmetric hydrogenation of prochiral halogenated ketones was successfully developed to prepare various chiral halohydrins with high reactivities and excellent enantioselectivities under basic reaction condition (up to >99% conversion, 99% yield, >99% ee). Moreover, gram-scale experiment was performed well in the presence of just 0.005 mol% (S/C=20 000) Ir/f-amphox catalyst with 99% yield and >99% ee. (Figure presented.).