174754-56-4

Basic information

• Product Name: (S)-A-HYDROXY-3-THIOPHENEACETONITRILE
• Synonyms: (S)-A-HYDROXY-3-THIOPHENEACETONITRILE
• CAS NO: 174754-56-4
• Molecular Formula: C6H5NOS
• Molecular Weight: 0
• Mol File: 174754-56-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-A-HYDROXY-3-THIOPHENEACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-A-HYDROXY-3-THIOPHENEACETONITRILE(174754-56-4)
• EPA Substance Registry System: (S)-A-HYDROXY-3-THIOPHENEACETONITRILE(174754-56-4)

Safety Data

• Hazardous Substances Data: 174754-56-4(Hazardous Substances Data)

Usage

General Description

(S)-A-HYDROXY-3-THIOPHENEACETONITRILE is a chemical compound with the molecular formula C6H5NOS, containing a thiophene ring and a nitrile functional group. It is a chiral compound with a stereochemistry denoted by the (S)- prefix. (S)-A-HYDROXY-3-THIOPHENEACETONITRILE has potential applications in pharmaceutical and agrochemical industries, as well as in the synthesis of organic compounds. Its specific properties and applications are under investigation and development in various fields of research and industry.

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 773837-37-9 sodium cyanide 
• 74-90-8 hydrogen cyanide 

Relevant articles and documents

A simple separation method for (S)-hydroxynitrile lyase from cassava and its application in asymmetric cyanohydrination

Using an acetone precipitation method, crude (S)-hydroxynitrile lyase [(S)-MeHNL] was separated from Munihot esculenta (cassava) leaves, and used directly as biocatalyst to catalyze asymmetric cyanohydrination and produce cyanohydrins with enantiomeric purities (≥90% ee) significantly greater than those previously reported. The use of a water/i-Pr2O system with an enzyme, NaCN, and appropriate amounts of acetic acid is crucial in improving the stereoselectivity of cyanohydrin formation by minimizing the non-enzymatic reaction and the racemization of the chiral products. The proposed isolation method for crude (S)-MeHNL has a high value because of its simplicity, and low cost as well as the high activity of the crude (S)-MeHNL.

Stereoselective synthesis of thienyl and furyl analogues of ephedrine

The stereoselective syntheses of thienyl and furyl analogues of ephedrine starting from (R)- and (S)-cyanohydrins, respectively, are described. Addition of methyl Grignard to the O-trimethylsilyl protected optically active cyanohydrins (R)- and (S)-3 and hydrogenation of the resulting imino intermediates gives the erythro-2-amino alcohols 4 with high diastereoselectivity. Their reductive methylation leads to the enantiomerically pure thiophene analogues (1S,2S)- and (1R,2R)-6a, (1R,2S)- and (1S,2R)-6b as well as to the furan analogues (1S,2S)-6c and (1R,2S)-6d of ephedrine, The biological activity of the new compounds is under investigation.