415679-40-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-1-(2,4-dichlorophenyl)ethan-1-ol is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
(R)-1-(2,4-dichlorophenyl)ethan-1-ol is also utilized in the production of agrochemicals, playing a role in the creation of substances that can enhance crop protection and yield.
Used in Fragrance Industry:
(R)-1-(2,4-dichlorophenyl)ethan-1-ol serves as a valuable component in the fragrance industry, where it is employed to develop new and complex scents for various applications.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of organic chemistry, (R)-1-(2,4-dichlorophenyl)ethan-1-ol is used as a chiral auxiliary to facilitate asymmetric synthesis, which is crucial for producing enantiomerically pure compounds with specific biological activities.
Used as a Precursor in Chemical Production:
Furthermore, (R)-1-(2,4-dichlorophenyl)ethan-1-ol acts as a precursor in the production of other chemicals, highlighting its importance in the broader chemical industry.
Overall, (R)-1-(2,4-dichlorophenyl)ethan-1-ol is a multifaceted compound with applications across different industries, including pharmaceuticals, agrochemicals, fragrances, and organic synthesis, due to its chemical versatility and structural uniqueness.

Upstream product

• 555-31-7 aluminum isopropoxide 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 60-29-7 diethyl ether 
• 29898-32-6 2,4-dichloro-1-iodo-benzene 
• 7553-56-2 iodine 
• 541-73-1 1,3-Dichlorobenzene 
• 13692-15-4 2-(2,4-dichlorophenyl)oxirane 
• 937-20-2 p-chlorophenacyl chloride 
• 1475-13-4 2,4-dichloro-α-methylbenzyl alcohol 
• 60907-89-3 2,4-dichloro-1-(1-chloroethyl)benzene 
• 672-65-1 (1-chloroethyl)benzene 
• 98-85-1 1-Phenylethanol 
• 20444-01-3 1-(1-bromoethyl)-2,4-dichlorobenzene 
• 75-07-0 acetaldehyde 

Downstream Products

• 20444-01-3 1-(1-bromoethyl)-2,4-dichlorobenzene 
• 478868-68-7 ethyl 4-(2,4-dichlorophenyl)-2,4-dioxobutyrate 
• 159427-17-5 ethyl 5-(2,4-dichlorophenyl)isoxazole-3-carboxylate 
• 925007-08-5 (5-(2,4-dichlorophenyl)isoxazol-3-yl)methanol 
• 1442445-14-8 ((S)-4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)-2-(hydroxymethyl)piperazin-1-yl)((R)-pyrrolidin-2-yl)methanone 
• 1442445-59-1 (R)-tert-butyl 2-((S)-4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)-2-(hydroxymethyl)piperazine-1-carbonyl)pyrrolidine-1-carboxylate 
• 1442445-75-1 ((S)-4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)piperazin-2-yl)methanol 
• 1442445-58-0 (S)-tert-butyl 4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)-2-(hydroxymethyl)piperazine-1-carboxylate 
• 1442445-13-7 ((R)-4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)-2-methylpiperazin-1-yl)((R)-pyrrolidin-2-yl)methanone 
• 1442445-57-9 (R)-tert-butyl 2-((R)-4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)-2-methylpiperazine-1-carbonyl)pyrrolidine-1-carboxylate 
• 1442445-74-0 1-((R)-1-(2,4-dichlorophenyl)ethyl)-6-((R)-3-methylpiperazin-1-yl)-1H-indazole 
• 1442445-56-8 C₂₅H₃₀Cl₂N₄O₂ 
• 1442445-12-6 (4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)piperazin-1-yl)((R)-pyrrolidin-2-yl)methanone 
• 1442445-55-7 (R)-tert-butyl 2-(4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-indazol-6-yl)piperazine-1-carbonyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Enhancing cofactor regeneration of cyanobacteria for the light-powered synthesis of chiral alcohols

Cyanobacteria Synechocystis sp. PCC 6803 was exploited as green cell factory for light-powered asymmetric synthesis of aromatic chiral alcohols. The effect of temperature, light, substrate and cell concentration on substrate conversions were investigated. Under the optimal condition, a series of chiral alcohols were synthesized with conversions up to 95% and enantiomer excess (ee) > 99%. We found that the addition of Na2S2O3 and Angeli's Salt increased the NADPH content by 20% and 25%, respectively. As a result, the time to reach 95% substrate conversion was shortened by 12 h, which demonstrated that the NADPH regeneration and hence the reaction rates can be regulated in cyanobacteria. This blue-green algae based biocatalysis showed its potential for chiral compounds production in future.

Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.

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.

Pincerlike molybdenum complex and preparation method thereof, catalytic composition and application thereof, and alcohol preparation method

The invention discloses a clamp-type molybdenum complex, a preparation method, a corresponding catalyst composition and application. The method comprises the steps: obtaining 9 molybdenum complexes with different structures through coordination reaction of 2-(substituent ethyl)-(5, 6, 7, 8-tetrahydroquinolyl) amine and a corresponding carbonyl molybdenum metal precursor; and catalyzing a ketone compound transfer hydrogenation reaction through a molybdenum complex to generate 40 alcohol compounds. The preparation method of the molybdenum complex is simple, high in yield and good in stability. For a transfer hydrogenation reaction of ketone, the molybdenum-based catalytic system has high catalytic activity and small molybdenum loading capacity, is used for production of aromatic and aliphatic alcohols, and has the advantages of simple method, small environmental pollution and high yield.

Ruthenium complexes of phosphine-amide based ligands as efficient catalysts for transfer hydrogenation reactions

This work presents three mononuclear Ru(ii) complexes of tridentate phosphine-carboxamide based ligands providing a NNP coordination environment. The octahedral Ru(ii) ion shows additional coordination with co-ligands; CO, Cl and CH3OH. All three Ru(ii) complexes were thoroughly characterized including their crystal structures. These Ru(ii) complexes were utilized as catalysts for the transfer hydrogenation of assorted carbonyl compounds, including some challenging biologically relevant substrates, using isopropanol as the hydrogen source. The binding studies illustrated the coordination of the isopropoxide ion by replacing a Ru-ligated chloride ion followed by the generation of the Ru-H intermediate that was isolated and characterized and was found to be involved in the catalysis.

1,3,4-Oxadiazole-functionalizedα-amino-phosphonates as ligands for the ruthenium-catalyzed reduction of ketones

Threeα-aminophosphonates, namely diethyl[(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl) methyl]phosphonate (3a), diethyl[(5-phenyl-1,3,4-oxadiazol-2-ylamino)(2-methoxyphenyl)methyl]phosphonate (3b) and diethyl[(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-nitrophenyl)methyl]phosphonate (3c), were synthetizedviathe Pudovik-type reaction between diethyl phosphite and imines, obtained from 5-phenyl-1,2,4-oxadiazol-2-amine and aromatic aldehydes, under microwave irradiation. Compounds3a-cunderwent complexation with a ruthenium(ii) precursor, selectively at the more basic nitrogen atom of the oxadiazole ring, leading to the corresponding ruthenium complexes4a-cof the formula [RuCl2(L)(p-cymene)] (L= α-aminophosphonates3a-c). Complexes4a-cproved to be efficient catalysts for the transfer hydrogenation of ketones to alcohols. All new compounds were fully characterised by elemental analysis, infrared, mass and NMR spectroscopy. An X-ray structure of the α-aminophosphonate3bwas obtained and revealed the presence, in the solid state, of an infinite chain of3bunits supramolecularly interlinked. Two X-ray diffraction studies carried out on ruthenium complexes confirm the specific coordination of the electron-enricher nitrogen atom of the oxadiazole ring.

Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand

A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable 'side arm' groups have been established, enabling the inexpensive base-promoted asymmetric hydrogenation of simple ketones with outstanding activities (up to 8200 TON) and good enantioselectivities (up to 88.5percent ee). This protocol features wide substrate scope and functional group tolerance, thereby providing easy access to a key intermediate of crizotinib.

Optimisation, scope and advantages of the synthesis of chiral phenylethanols using whole seeds of Bauhinia variegata L. (Fabaceae) as a new and stereoselective bio-reducer of carbonyl compounds

With the aim of finding new methods for environmentally friendly synthesis of chiral phenylethanols, a screening was carried out to identify seeds that could be used as a biocatalyst capable of reducing stereoselectively prochiral ketones. As a result, seeds of Bauhinia variegata L. (Fabaceae) were identified as being an efficient and stereoselective biological reducer of acetophenone to produce (S)-1-phenylethanol (conversion of 98% and 99 e.e.%). Then, to optimise the reductive process, the effects of some variables such as temperature, load of substrate, pH, co-solvent, and reuse and storability of the seeds as a function of time were established. Utilising the optimal reaction conditions, nineteen substituted acetophenones were reduced to their corresponding chiral alcohols with a conversion ranging from 30% to 98% and enantiomeric excess of between 65% and >99%, and in addition, useful key intermediates were also obtained by the synthesis of drugs. The scope and advantages of this new biocatalytic synthetic method are also discussed.Research highlights A screening was carried out to identify seeds that could be used as a biocatalyst Seeds of Bauhinia variegata have been identified as an efficient biocatalyst to reduce carbonyl compounds. Acetophenone and substituted acetophenones were reduced with high stereoselectivity. Some key intermediates were synthetised using this methodology. Seeds can be stored for twenty-four months without loss of activity.

Transfer Hydrogenation of Ketones and Imines with Methanol under Base-Free Conditions Catalyzed by an Anionic Metal-Ligand Bifunctional Iridium Catalyst

An anionic iridium complex [Cp*Ir(2,2′-bpyO)(OH)][Na] was found to be a general and highly efficient catalyst for transfer hydrogenation of ketones and imines with methanol under base-free conditions. Readily reducible or labile substituents, such as nitro, cyano, and ester groups, were tolerated under present reaction conditions. Notably, this study exhibits the unique potential of anionic metal-ligand bifunctional iridium catalysts for transfer hydrogenation with methanol as a hydrogen source.

Aza-crown compounds synthesised by the self-condensation of 2-amino-benzyl alcohol over a pincer ruthenium catalyst and applied in the transfer hydrogenation of ketones

A well-defined PNN-Ru catalyst was revisited to self-condense 2-aminobenzyl alcohol in forming a series of novel aza-crown compounds [aza-12-crown-3 (1), aza-16-crown-4 (2) and aza-20-crown-5 (3)]. All aza-crown compounds are separated and determined by NMR, IR, and ESI-MS spectroscopy as well as X-ray crystallography, indicating the saddle structure of 1 and the twisted 1,3-alternate conformation structure of 3. These aza-crown compounds have been explored to study ferric initiation of transfer hydrogenation (TH) of ketones into their corresponding secondary alcohols in the presence of 2-propanol with a basic t-BuOK solution, achieving a high conversion (up to 95%) by a ferric complex with 2 in a low loading (0.05 mol%). This journal is