134562-59-7

Basic information

• Product Name: (S)-A-HYDROXY-2-THIOPHENEACETONITRILE
• Synonyms: (S)-A-HYDROXY-2-THIOPHENEACETONITRILE
• CAS NO: 134562-59-7
• Molecular Formula: C6H5NOS
• Molecular Weight: 139.18
• Mol File: 134562-59-7.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-A-HYDROXY-2-THIOPHENEACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-A-HYDROXY-2-THIOPHENEACETONITRILE(134562-59-7)
• EPA Substance Registry System: (S)-A-HYDROXY-2-THIOPHENEACETONITRILE(134562-59-7)

Safety Data

• Hazardous Substances Data: 134562-59-7(Hazardous Substances Data)

Usage

General Description

(S)-A-HYDROXY-2-THIOPHENEACETONITRILE is a chemical compound with the molecular formula C6H5NOS and a molecular weight of 147.18 g/mol. It is a thienylacetonitrile derivative with a hydroxy group positioned at the stereogenic center, leading to its chiral nature. (S)-A-HYDROXY-2-THIOPHENEACETONITRILE is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals due to its versatile reactivity and synthetic potential. Its ability to undergo various organic reactions, such as nucleophilic addition, substitution, and elimination, makes it a valuable building block in the production of complex organic molecules. Additionally, (S)-A-HYDROXY-2-THIOPHENEACETONITRILE is known for its potential biological and pharmacological activities, making it an area of interest for medicinal and pharmaceutical research. Overall, this compound plays a significant role in organic synthesis and drug discovery processes.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 
• 89380-68-7 2-hydroxy-2-(thiophen-2-yl)acetonitrile 
• 188481-46-1 (S)-Thiophen-2-yl-trimethylsilanyloxy-acetonitrile 

Downstream Products

• 116539-55-0 (S)-3-methylamino-1-(2-thienyl)-1-propanol 
• 116539-60-7 (R)-Duloxetine 

Relevant articles and documents

A High-Throughput Screening Method for the Directed Evolution of Hydroxynitrile Lyase towards Cyanohydrin Synthesis

Chiral cyanohydrins are useful intermediates in the pharmaceutical and agricultural industries. In nature, hydroxynitrile lyases (HNLs) are a kind of elegant tool for enantioselective hydrocyanation of carbonyl compounds. However, currently available methods for demonstrating hydrocyanation are still stalled at precise, but low-throughput, GC or HPLC analyses. Herein, we report a chromogenic high-throughput screening (HTS) method that is feasible for the cyanohydrin synthesis reaction. This method was highly anti-interference and sensitive, and could be used to directly profile the substrate scope of HNLs either in cell-free extract or fermentation clear broth. This HTS method was also validated by generating new variants of PcHNL5 that presented higher catalytic efficiency and stronger acidic tolerance in variant libraries.

Supported Ionic Liquid-Like Phases (SILLPs) as Immobilised Catalysts for the Multistep and Multicatalytic Continuous Flow Synthesis of Chiral Cyanohydrins

Supported Ionic Liquid-Like Phases have been found to be efficient organocatalysts for the synthesis of cyanohydrin esters under solvent-free conditions by an “electrophile-nucleophile dual activation” based on hydrogen bond formation. The combination of

Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications

Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).