153225-88-8

Basic information

• Product Name: (R)-4-(2-PROPENYLOXY)-MANDELONITRILE
• Synonyms: (R)-4-(2-PROPENYLOXY)-MANDELONITRILE
• CAS NO: 153225-88-8
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Mol File: 153225-88-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-4-(2-PROPENYLOXY)-MANDELONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-(2-PROPENYLOXY)-MANDELONITRILE(153225-88-8)
• EPA Substance Registry System: (R)-4-(2-PROPENYLOXY)-MANDELONITRILE(153225-88-8)

Safety Data

• Hazardous Substances Data: 153225-88-8(Hazardous Substances Data)

Usage

General Description

"(R)-4-(2-propenyloxy)-mandelonitrile" is a chemical compound with the molecular formula C10H9NO2. It is a nitrile derivative of mandelic acid and possesses a chiral center, leading to the existence of its enantiomer, (S)-4-(2-propenyloxy)-mandelonitrile. (R)-4-(2-PROPENYLOXY)-MANDELONITRILE is used in the synthesis of pharmaceuticals and agrochemicals, as well as in the production of perfumes and flavorings. It is also a key intermediate in the manufacturing of various organic compounds, including those used in the development of new materials and bioactive agents. Additionally, (R)-4-(2-propenyloxy)-mandelonitrile has potential applications in the field of organic chemistry as a building block for the construction of complex molecules with specific stereochemical properties.

Upstream product

• 74-90-8 hydrogen cyanide 
• 40663-68-1 4-(2-propenyloxy)benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 151-50-8 potassium cyanide 

Downstream Products

• 153225-90-2 (-)-(α)-<<<2-(3,4-dimethoxyphenyl)ethyl>amino>methyl>-(α)-<(1,1-dimethylethyl)dimethylsilyloxy>-4-(2-propenyloxy)benzenemethane 
• 153225-91-3 (-)-(α)-<<<2-(3,4-dimethoxyphenyl)ethyl>amino>methyl>-4-(2-propenyloxy)benzenemethanol 
• 71771-90-9 denopamine 
• 153225-89-9 (R)-2-<(1,1-dimethylethyl)dimethylsilyloxy>-2-<4-(2-propenyloxy)phenyl>acetonitrile 

Relevant articles and documents

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

Substituent Effects on the Enantioselective Hydrocyanation of Aryl Aldehydes

A detailed study of the dipeptide catalysed enantioselective hydrocyanation of a series of O-substituted 4-hydroxybenzaldehydes has shown that adverse steric effects can occur leading to low enantiomeric excess (e.e.) values when the substituent is long and flexible.Similar hydrocyanation of several derivatives of 3,4-dihydroxybenzaldehydes have been shown to give very variable values of e.e.Hydrocyanation of 3,5-dimethoxy and 3,4,5-trimethoxybenzaldehyde consistently gave low values of e.e.

A Synthesis of (-)-Denopamine

The important cardiac drug, (-)-denopamine, has been synthesized in 68percent overall yield from para-allyloxybenzaldehyde via (R)-2-hydroxy-2-acetonitrile.