10049-64-6

Basic information

• Product Name: (R)-(+)-3-HYDROXYMANDELONITRILE
• Synonyms: (R)-(+)-3-HYDROXYMANDELONITRILE
• CAS NO: 10049-64-6
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 0
• Mol File: 10049-64-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(+)-3-HYDROXYMANDELONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-3-HYDROXYMANDELONITRILE(10049-64-6)
• EPA Substance Registry System: (R)-(+)-3-HYDROXYMANDELONITRILE(10049-64-6)

Safety Data

• Hazardous Substances Data: 10049-64-6(Hazardous Substances Data)

Usage

General Description

(R)-(+)-3-Hydroxymandelonitrile is a chemical compound with the molecular formula C8H7NO2. It is an organic compound that is commonly used in the synthesis of pharmaceuticals and agrochemicals. (R)-(+)-3-Hydroxymandelonitrile is a chiral compound and exists in two enantiomeric forms, with the (R)-enantiomer exhibiting optical activity. It is a key intermediate in the synthesis of various medications and has been studied for its potential pharmacological properties. The compound has also been used in the development of new synthetic methods and as a building block in organic synthesis.

Upstream product

• 74-90-8 hydrogen cyanide 
• 100-83-4 meta-hydroxybenzaldehyde 

Relevant articles and documents

Synthesis of the Adrenergic Bronchodilators (R)-Terbutalinel and (R)-Salbutamol from (R)-Cyanohydrins

Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9·HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of (A)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (A)-7b and c to (R)-salbutamol was not yet possible without racemization.