134356-70-0

Basic information

• Product Name: (R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol
• Synonyms: 2-chloro-1-(4-methoxyphenyl)ethanol
• CAS NO: 134356-70-0
• Molecular Weight: 0
• Mol File: 134356-70-0.mol
• Article Data: 37

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol(134356-70-0)
• EPA Substance Registry System: (R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol(134356-70-0)

Safety Data

• Hazardous Substances Data: 134356-70-0(Hazardous Substances Data)

Usage

Description

(R)-2-Chloro-1-(4-Methoxyphenyl) Ethanol is a chemical compound characterized by a chloro-substituted ethanol group connected to a phenyl ring with a methoxy substituent. It is recognized for its potential as a chiral building block in the synthesis of pharmaceuticals and biologically active molecules, making it a valuable asset in organic synthesis and pharmaceutical research.

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

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

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 
• 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 
• 920797-21-3 N-benzyl-2-chloro-N-[(2S)-2-(4-fluorophenyl)-2-hydroxyethyl]acetamide 
• 503860-58-0 (2S)-2-(4-fluorophenyl)morpholine hydrochloride 
• 920796-74-3 (2S)-4-benzyl-2-(4-fluorophenyl)morpholine 
• 503860-57-9 UDA-680 
• 920796-73-2 (6S)-6-(4-fluorophenyl)-4-benzylmorpholine-3-one 

Relevant articles and documents

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.

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.

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.