112653-32-4

Basic information

• Product Name: (S)-(-)-1-(2-FURYL)ETHANOL
• Synonyms: (S)-(-)-1-(2-FURYL)ETHANOL;(S)-1-(2-FURYL)ETHANOL;S(-)-2-FURYL METHYL CARBINOL;S(-)-ALPHA-METHYLFURAN-2-METHANOL;(S)-1-(furan-2-yl)ethanol
• CAS NO: 112653-32-4
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13
• Mol File: 112653-32-4.mol
• Article Data: 167

Chemical Properties

• Boiling Point: 60-61 °C8 mm Hg(lit.)
• Flash Point: 34.6 °C
• Appearance: /
• Density: 1.078 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.479
• Storage Temp.: −20°C
• CAS DataBase Reference: (S)-(-)-1-(2-FURYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-(2-FURYL)ETHANOL(112653-32-4)
• EPA Substance Registry System: (S)-(-)-1-(2-FURYL)ETHANOL(112653-32-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 112653-32-4(Hazardous Substances Data)

Usage

Description

(S)-(-)-1-(2-FURYL)ETHANOL, also known as (S)-1-(Furan-2-yl)ethanol, is an organic compound with a unique structure that features a furan ring and an ethanol group. It is a chiral molecule, which means it exists in two different forms that are mirror images of each other, known as enantiomers. The (S)-(-)-1-(2-FURYL)ETHANOL is one of these enantiomers, characterized by its specific spatial arrangement of atoms.

Uses

Used in Enzymatic Synthesis:
(S)-(-)-1-(2-FURYL)ETHANOL is used as a reagent in the lipase-catalyzed asymmetric acylation of furan-based alcohols. This application takes advantage of the compound's unique structure and chirality, allowing for the selective synthesis of specific enantiomers with the help of lipase enzymes. The process is valuable in the production of enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals and agrochemicals, where the desired biological activity is often associated with a single enantiomer.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-(-)-1-(2-FURYL)ETHANOL can be used as a building block or intermediate for the synthesis of chiral drugs. The compound's unique structure and enantiomeric purity make it a valuable starting material for the development of new drugs with improved efficacy and reduced side effects.
Used in Flavor and Fragrance Industry:
(S)-(-)-1-(2-FURYL)ETHANOL may also find applications in the flavor and fragrance industry due to its distinct chemical properties. The compound could be used to create novel scents or enhance existing ones, contributing to the development of new products with unique sensory profiles.
Used in Chemical Research:
As a chiral molecule with a furan ring, (S)-(-)-1-(2-FURYL)ETHANOL can be a valuable tool in chemical research, particularly in the study of asymmetric synthesis, catalysis, and the development of new synthetic methods. Researchers can use this compound to explore various reaction pathways and develop new strategies for the synthesis of complex molecules with potential applications in various industries.

Upstream product

• 98-01-1 furfural 
• 544-97-8 dimethyl zinc(II) 
• 75-16-1 methylmagnesium bromide 
• 74-88-4 methyl iodide 
• 4208-64-4 1-(2-furyl)ethanol 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 113531-28-5 Octanoic acid 1-furan-2-yl-ethyl ester 
• 1487-18-9 (furan-2-yl)ethylene 
• 108-22-5 Isopropenyl acetate 
• 209682-89-3 1-ethoxyvinyl methyl fumarate 
• 638-11-9 isopropyl butyrate 
• 101-41-7 benzeneacetic acid methyl ester 
• 108-05-4 vinyl acetate 
• 117-34-0 2,2-diphenylacetic acid 

Downstream Products

• 33647-67-5 (S)-1-(2,5-dihydro-2,5-dimethoxy-2-furyl)ethanol 
• 201279-57-4 (S)-benzoic acid 1-furan-2-yl-ethyl ester 
• 266323-47-1 (S)-1-(2-furyl)-1-(4-methoxybenzyloxy)ethane 
• 735315-15-8 Kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranoside) 
• 910041-19-9 (2S,3R,4R,5S,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 916069-02-8 3-((2S,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 916069-03-9 3-((2S,5R,6S)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 916069-05-1 6-(5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yloxy)-3,6-dihydro-2-methyl-2H-pyran-3-yl acetate 
• 916069-04-0 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one 
• 916069-06-2 (2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate 
• 916069-07-3 (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate 
• 916069-08-4 (2S,3S,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yl)oxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate 
• 482-39-3 kaempferol 3-rhamnoside 
• 135618-17-6 Kaempferol-3-O-(4-O-acetyl-alpha-L-rhamnopyranoside) 

Relevant articles and documents

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.

Phase Separation-Promoted Redox Deracemization of Secondary Alcohols over a Supported Dual Catalysts System

Unification of oxidation and reduction in a one-pot deracemization process has great significance in the preparation of enantioenriched organic molecules. However, the intrinsic mutual deactivation of oxidative and reductive catalysts and the extrinsic incompatible reaction conditions are unavoidable challenges in a single operation. To address these two issues, we develop a supported dual catalysts system to overcome these conflicts from incompatibility to compatibility, resulting in an efficient one-pot redox deracemization of secondary alcohols. During this transformation, the TEMPO species onto the outer surface of silica nanoparticles catalyze the oxidation of racemic alcohols to ketones, and the chiral Rh/diamine species in the nanochannels of the thermoresponsive polymer-coated hollow-shell mesoporous silica enable the asymmetric transfer hydrogenation (ATH) of ketones to chiral alcohols. To demonstrate the general feasibility, a series of orthogonal oxidation/ATH cascade reactions are compared to prove the compatible benefits in the elimination of their deactivations and the balance of the cascade directionality. As presented in this study, this redox deracemization process provides various chiral alcohols with enhanced yields and enantioselectivities relative to those from unsupported dual catalysts systems. Furthermore, the dual catalysts can be recycled continuously, making them an attractive feature in the application.

Palladium-Catalyzed Regioselective and Diastereoselective C-Glycosylation by Allyl-Allyl Coupling

A Pd-catalyzed C-glycosylation reaction was developed by allyl-allyl coupling process using Achmatowicz rearrangement products as donors and methylcoumarins as acceptors under mild conditions. This method featured regio- and diastereoselectivities, stereo