7606-26-0

Basic information

• Product Name: (R)-1-(3-PYRIDYL)ETHANOL
• Synonyms: (R)-1-(3-PYRIDYL)ETHANOL;(R)-3-(1-HYDROXYETHYL)PYRIDINE;(1R)-1-(3-Pyridyl)ethanol;(R)-α-Methylpyridine-3-methanol;(αR)-α-Methylpyridine-3-methanol;[R,(+)]-α-Methyl-3-pyridinemethanol;(aR)-a-Methyl-3-PyridineMethanol;(R)-1-(Pyridin-3-yl)ethanol
• CAS NO: 7606-26-0
• Molecular Formula: C₇H₈NO*H
• Molecular Weight: 123.15
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;API intermediates
• Mol File: 7606-26-0.mol

Chemical Properties

• Boiling Point: 239.602 °C at 760 mmHg
• Flash Point: 98.708 °C
• Appearance: /
• Density: 1.083 g/cm³
• Vapor Pressure: 0.022mmHg at 25°C
• Refractive Index: 1.535
• PKA: 13.75±0.20(Predicted)
• CAS DataBase Reference: (R)-1-(3-PYRIDYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(3-PYRIDYL)ETHANOL(7606-26-0)
• EPA Substance Registry System: (R)-1-(3-PYRIDYL)ETHANOL(7606-26-0)

Safety Data

• Hazardous Substances Data: 7606-26-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(3-Pyridyl)ethanol is used as a chiral building block for the production of drugs that target central nervous system disorders, cancer, and infectious diseases. Its chiral nature allows for the creation of enantiomerically pure compounds, which is essential for the development of effective and safe medications.
Used in Agrochemical Industry:
(R)-1-(3-Pyridyl)ethanol is used as a precursor in the synthesis of agrochemicals, contributing to the development of more effective and environmentally friendly pesticides and herbicides.
Used in Fine Chemicals Industry:
(R)-1-(3-Pyridyl)ethanol is utilized as a key intermediate in the production of various fine chemicals, including fragrances, dyes, and other specialty chemicals.
Used as a Chiral Resolving Agent:
(R)-1-(3-Pyridyl)ethanol is employed as a chiral resolving agent in the separation of enantiomers, which is crucial for obtaining pure compounds with desired biological activities.
Used as a Ligand in Asymmetric Catalysis:
(R)-1-(3-Pyridyl)ethanol serves as a ligand in asymmetric catalysis, enabling the selective synthesis of enantiomerically pure compounds with high yields and selectivity.
Used in Material Science:
(R)-1-(3-Pyridyl)ethanol has potential applications in the development of new materials, such as chiral polymers and other advanced materials with unique properties.
Used in Organic Chemistry Research:
(R)-1-(3-Pyridyl)ethanol is a valuable compound for researchers in the field of organic chemistry, as it can be used to explore new synthetic routes, reaction mechanisms, and the development of novel catalysts and reagents.

InChI:InChI=1/C7H9NO/c1-6(9)7-3-2-4-8-5-7/h2-6,9H,1H3/t6-/m1/s1

Upstream product

• 350-03-8 methyl-3-pyridylketone 
• 4754-27-2 1-(3-Pyridyl)ethanol 
• 35692-86-5 1-(3-Pyridyl)ethyl acetate 
• 27854-86-0 (1R)-1-(3-pyridyl)ethyl acetate 
• 500-22-1 3-pyridinecarboxaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 67031-82-7 1-(3-Pyridyl)ethyl benzoate 
• 536-78-7 3-ethylpyridine 
• 67-63-0 isopropyl alcohol 
• 108-05-4 vinyl acetate 
• 97-72-3 2-Methylpropionic anhydride 
• 75-24-1 trimethylaluminum 

Downstream Products

• 183866-66-2 (R)-3-Eth-(Z)-ylidene-4-(1H-indol-2-ylmethyl)-piperidine-1-carboxylic acid benzyl ester 
• 183866-63-9 (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate 
• 183866-61-7 5-((R)-1-Hydroxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 72504-66-6 (1R)-1-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)ethanol 

Relevant articles and documents

Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity

A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.

Manganese catalyzed asymmetric transfer hydrogenation of ketones

The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol% of catalyst loading, affording highly valuable chiral alcohols with up to 95% ee.

Ruthenium-catalyzed hydrogenation of aromatic ketones using chiral diamine and monodentate achiral phosphine ligands

The Ru-catalyzed asymmetric hydrogenation of ketones with chiral diamine and monodentate achiral phosphine has been developed. A wide range of ketones were hydrogenated to afford the corresponding chiral secondary alcohols in good to excellent enantioselectivities (up to 98.1% ee). In addition, an appropriate mechanism for the asymmetric hydrogenation was proposed and verified by NMR spectroscopy.

C1-Symmetric PNP Ligands for Manganese-Catalyzed Enantioselective Hydrogenation of Ketones: Reaction Scope and Enantioinduction Model

A family of ferrocene-based chiral PNP ligands is reported. These tridentate ligands were successfully applied in Mn-catalyzed asymmetric hydrogenation of ketones, giving high enantioselectivities (92%～99% ee for aryl alkyl ketones) as well as high efficiencies (TON up to 2000). In addition, dialkyl ketones could also be hydrogenated smoothly. Manganese intermediates that might be involved in the catalytic cycle were analyzed. DFT calculation was carried out to help understand the chiral induction model. The Mn/PNP catalyst could discriminate two groups with different steric properties by deformation of the phosphine moiety in the flexible 5-membered ring.

RETRACTED ARTICLE: The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase: Sm ADH2 via an environmentally friendly TBCR system

Alcohol dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asymmetric synthesis of chiral alcohols; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the by-product, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technology. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, v/v) concentration. Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the by-product acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcohols are synthesised at a high substrate loading (>150 g L-1) without adding external coenzymes. Among these, about 780 g L-1 (6 M) ethyl acetoacetate is completely converted into ethyl (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L-1 d-1 space-time yield. Molecular dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcohols on an industrial scale.

Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System

Bioreductions catalyzed by alcohol dehydrogenases (ADHs) play an important role in the synthesis of chiral alcohols. However, the synthesis of ethyl (S)-4-chloro-3-hydroxybutyrate [(S)-CHBE], an important drug intermediate, has significant challenges concerning high substrate or product inhibition toward ADHs, which complicates its production. Herein, we evaluated a novel ADH, SmADH31, obtained from the Stenotrophomonas maltophilia genome, which can tolerate extremely high concentrations (6 M) of both substrate and product. The coexpression of SmADH31 and glucose dehydrogenase from Bacillus subtilis in Escherichia coli meant that as much as 660 g L-1 (4.0 M) ethyl 4-chloroacetoacetate was completely converted into (S)-CHBE in a monophasic aqueous system with a >99.9% ee value and a high space-time yield (2664 g L-1 d-1). Molecular dynamics simulation shed light on the high activity and stereoselectivity of SmADH31. Moreover, five other optically pure chiral alcohols were synthesized at high concentrations (100-462 g L-1) as a result of the broad substrate spectrum of SmADH31. All these compounds act as important drug intermediates, demonstrating the industrial potential of SmADH31-mediated bioreductions.

Iridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and sp3-C?H Noncovalent Interactions

Iridium-catalyzed enantioselective transfer hydrogenation of ketones with formic acid was developed using a prolinol-phosphine chiral ligand. Cooperative action of the iridium atom and the ligand through alcohol-alkoxide interconversion is crucial to facilitate the transfer hydrogenation. Various ketones including alkyl aryl ketones, ketoesters, and an aryl heteroaryl ketone were competent substrates. An attractive feature of this catalysis is efficient discrimination between the alkyl and aryl substituents of the ketones, promoting hydrogenation with the identical sense of enantioselection regardless of steric demand of the alkyl substituent and thus resulting in a rare case of highly enantioselective transfer hydrogenation of tert-alkyl aryl ketones. Quantum chemical calculations revealed that the sp3-C?H/π interaction between an sp3-C?H bond of the prolinol-phosphine ligand and the aryl substituent of the ketone is crucial for the enantioselection in combination with O?H???O/sp3-C?H???O two-point hydrogen-bonding between the chiral ligand and carbonyl group. (Figure presented.).

A simple and efficient asymmetric hydrogenation of heteroaromatic ketones with iridium catalyst composed of chiral diamines and achiral phosphines

An efficient iridium catalyst composed of a simple and commercially available o-methoxytriphenylphosphine and 9-Amino (9-deoxy) epi-cinchonine was applied to the asymmetric hydrogenation of heteroaromatic ketones. A range of simple heteroaromatic ketones could be hydrogenated with good to excellent enantioselectivities and high activities. In particular, thiophene ketones and furyl ketones furnished 98.6% ee with up to 2.18 × 104(1/h) TOF. This catalytic system can be of practical value.

Enhanced activity and modified substrate-favoritism of Burkholderia cepacia lipase by the treatment with a pyridinium alkyl-PEG sulfate ionic liquid

Three types of pyridinium salts, i.e., 1-ethylpyridin-1-ium cetyl-PEG10 sulfate (PYET), 1-butylpyridin-1-ium cetyl-PEG10 sulfate (PYBU), and 1-(3-methoxypropyl)pyridin-1-ium cetyl-PEG10 sulfate (PYMP), have been prepared and evaluated for their activation property of Burkholderia cepacia lipase by comparison to the control IL-coated enzymes, 1-butyl-2,3-dimethylimidazolium cetyl-PEG10 sulfate-coated lipase PS (IL1-PS). Among the tested pyridinium salt-coated lipases, the PYET-coated lipase PS (PYET-PS) exhibited the best results; the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, 1-(pyridin-4-yl)ethanol, or 4-phenylbut-3-en-2-ol proceeded faster than those of the IL1-PS-catalyzed reaction while maintaining an excellent enantioselectivity (E > 200). This improved efficiency was found to be dependent on the increased Kcat value.