121985-99-7

Basic information

• Product Name: (R)-2-METHOXYMANDELONITRILE
• Synonyms: (R)-2-METHOXYMANDELONITRILE
• CAS NO: 121985-99-7
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 0
• Mol File: 121985-99-7.mol
• Article Data: 45

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-METHOXYMANDELONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-METHOXYMANDELONITRILE(121985-99-7)
• EPA Substance Registry System: (R)-2-METHOXYMANDELONITRILE(121985-99-7)

Safety Data

• Hazardous Substances Data: 121985-99-7(Hazardous Substances Data)

Usage

General Description

"(R)-2-Methoxymandelonitrile" is a chemical compound with the molecular formula C9H9NO2. It is a chiral molecule, meaning it has a non-superimposable mirror image, and the (R)- designation indicates the stereochemistry of this particular molecule. (R)-2-METHOXYMANDELONITRILE is commonly used as an intermediate in the synthesis of various pharmaceuticals and fine chemicals. It is also known for its almond-like odor and is often used in the fragrance industry as a component in perfumes and cosmetics. Additionally, (R)-2-Methoxymandelonitrile has been studied for its potential anti-cancer properties and is being researched for its use in cancer treatment.

Upstream product

• 135-02-4 ortho-anisaldehyde 
• 151-50-8 potassium cyanide 
• 74-90-8 hydrogen cyanide 
• 82128-71-0 2-(2-methyloxyphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 773837-37-9 sodium cyanide 
• 4746-48-9 2-hydroxy-2,2-diphenylacetonitrile 
• 90-02-8 salicylaldehyde 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 143-33-9 sodium cyanide 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 92496-51-0 3-(2-methoxy-phenyl)-3H-benzofuran-2-one 
• 125237-16-3 p,p'-bis(α-cyano(2-methoxyphenyl)methylhydrazinocarbonylmethoxy)diphenyl sulphone 
• 72371-46-1 (2-methoxy-phenyl)-glyoxylonitrile 
• 93-25-4 2-methoxyphenylacetic acid 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 135-02-4 ortho-anisaldehyde 
• 89709-23-9 (R)-2-methoxymandelic acid 
• 96929-45-2 α-amino-2-methoxybenzeneacetonitrile 
• 1434652-66-0 (R)-2-(2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)ethan-1-ol 
• 1630859-22-1 2-(tert-butyldiphenylsilyloxy)-2-(2-methoxyphenyl)acetonitrile 
• 1476803-99-2 C₂₃H₂₀N₂O₄ 
• 26767-06-6 2-(2-methoxyphenyl)-2-oxoacetic acid 
• 1476804-82-6 C₂₃H₁₈N₂O₃ 
• 41873-63-6 (2-Carboxymethoxy-phenyl)-essigsaeure 

Relevant articles and documents

Enzyme Optimization and Process Development for a Scalable Synthesis of (R)-2-Methoxymandelic Acid

The rational protein engineering of wild type BCJ2315 nitrilase and its use in the development of a one-pot, enantioselective, dynamic kinetic resolution for (R)-2-methoxymandelic acid is reported. Through a combination of molecular docking and B-factor a

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

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.).