27948-39-6

Basic information

• Product Name: (1S)-1-(2-THIENYL)ETHANOL
• Synonyms: (S)-1-(THIOPHEN-2-YL)ETHANOL;(S)-1-(2-THIENYL)ETHANOL;(1S)-ALPHA-METHYL-2-THIOPHENEMETHANOL;(1S)-1-(2-THIENYL)ETHANOL;(1S)-1-(2-THIOPHENE)ETHANOL;(1S)-1-(2-THIOPHEN)ETHANOL;(1s)-α-methyl-2-thiophenemethanol
• CAS NO: 27948-39-6
• Molecular Formula: C₆H₈OS
• Molecular Weight: 128.19
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 27948-39-6.mol
• Article Data: 154

Chemical Properties

• Boiling Point: 212.8 °C at 760 mmHg
• Flash Point: 82.5 °C
• Appearance: /
• Density: 1.165 g/cm³
• Vapor Pressure: 0.101mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: 2-8°C
• PKA: 13.95±0.20(Predicted)
• CAS DataBase Reference: (1S)-1-(2-THIENYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-1-(2-THIENYL)ETHANOL(27948-39-6)
• EPA Substance Registry System: (1S)-1-(2-THIENYL)ETHANOL(27948-39-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 27948-39-6(Hazardous Substances Data)

Usage

Description

(1S)-1-(2-THIENYL)ETHANOL, also known as (S)-1-(Thiophen-2-yl)ethanol, is an organic compound characterized by its unique structure that features a thiophene ring attached to an ethanol group. (1S)-1-(2-THIENYL)ETHANOL is known for its distinct chemical properties and reactivity, making it a versatile building block in the synthesis of various complex molecules.

Uses

Used in Pharmaceutical Industry:
(1S)-1-(2-THIENYL)ETHANOL is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to be readily modified and incorporated into more complex molecular structures. Its unique thiophene ring provides a distinct set of chemical properties that can be exploited in the design of novel drugs.
Used in Chemical Synthesis:
(1S)-1-(2-THIENYL)ETHANOL is used as a building block in the chemical synthesis of various organic compounds, particularly those containing thiophene moieties. Its reactivity and compatibility with a wide range of synthetic methods make it a valuable component in the creation of diverse chemical libraries.
Used in Enzymatic Reactions:
(1S)-1-(2-THIENYL)ETHANOL is used as an intermediate in the lipase-catalyzed acylation of heteroaromatic alcohols with succinic anhydride. This application takes advantage of the compound's ability to participate in selective enzymatic reactions, which can lead to the production of specific target molecules with high efficiency and selectivity.

InChI:InChI=1/C6H8OS/c1-5(7)6-3-2-4-8-6/h2-5,7H,1H3/t5-/m0/s1

Upstream product

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Relevant articles and documents

Practical access to (S)-heterocyclic aromatic acetates via CAL-B/Na2CO3-deacylation and Mitsunobu reaction protocol

Herein, we report the preparation of enantiomerically pure forms of 2,3-dihydrobenzofuran-3-ol (1), chroman-4-ol (2), thiochroman-4-ol (3), 1-(furan-2-yl) ethanol (5) and 1-(thiophen-2-yl) ethanol (6), through a kinetic resolution catalysed by Candida antarctica lipase B/Na2CO3 hydrolysis sequence in organic media. The (R)-furnished alcohols and the (S)-remained acetates are recovered enantiopures (ee?>99%, E???200, Conv = 50%). Those ideal enzymatic kinetic resolution (EKRs) are well incorporated to the Mitsunobu inversion protocol in a one pot procedure to give (S)-heterocyclic acetates (1a–3a) in good to high enantiomeric excess (88%–92% ee). Whilst, the (S)-heteroaromatic acetates (5a and 6a) are given with moderate enantiomeric excess (51%–62% ee). All the (S)-acetates are given in good isolated chemical yields (>80%) allowing to overcome the maximum of 50% yield which could be usually reached in a regular kinetic resolution processes.

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.

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.