174849-23-1

Basic information

• Product Name: (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE
• Synonyms: (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE
• CAS NO: 174849-23-1
• Molecular Formula: C7H13NO
• Molecular Weight: 0
• Mol File: 174849-23-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE(174849-23-1)
• EPA Substance Registry System: (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE(174849-23-1)

Safety Data

• Hazardous Substances Data: 174849-23-1(Hazardous Substances Data)

Usage

General Description

(S)-2-Hydroxy-2,4-dimethyl-pentanenitrile is a chemical compound with the molecular formula C7H13NO. It is an organic nitrile, which is a compound containing a cyano group attached to a carbon atom. (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE is a chiral molecule, meaning it has different spatial arrangements of atoms that result in non-superimposable mirror images. It is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Additionally, it can also be used as an intermediate in the production of perfumes and flavoring agents. (S)-2-Hydroxy-2,4-dimethyl-pentanenitrile is a versatile compound with various applications in the chemical industry.

Upstream product

• 74-90-8 hydrogen cyanide 
• 108-10-1 4-methyl-2-pentanone 
• 4131-68-4 2-hydroxy-2,4-dimethylpentanenitrile 
• 151-50-8 potassium cyanide 
• 143-33-9 sodium cyanide 

Downstream Products

• 3639-23-4 2-hydroxy-2,4-dimethylpentanoic acid 
• 135415-91-7 (R)-2-hydroxy-2,4-dimethylpentanoic acid 
• 3639-23-4 (S)-2-hydroxy-2,4-dimethylpentanoic acid 

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).

Approach to (R)- and (S)-ketone cyanohydrins using almond and apple meal as the source of (R)-oxynitrilase

The synthesis of aliphatic and aromatic (R)-ketone cyanohydrins through the addition of hydrogen cyanide to the corresponding ketones and the synthesis of the (S)-enantiomers through the kinetic resolution of racemic ketone cyanohydrins has been studied in the presence of almond or apple meal. Substrate tolerance of the (R)-oxynitrilases towards ketones (R1R2C=O) is highly restricted compared to that of structurally similar aldehydes, reactivity following the order of H>Me>>Et for R2. In the case of aromatic methyl ketones reactivity difference (C6H5>>p-Me-C6H4 for R1) is notable.

(R)-Oxynitrilase Catalyzed Synthesis of (R)-Ketone Cyanohydrins

(R)-Oxynitrilase from almonds (Prunus amygdalus) catalyzed the enantioselective addition of HCN to ethyl alkyl ketones 1 in diisopropyl ether yielding (R)-ethyl alkyl ketone cyanohydrins (R)-2, which are hydrolyzed under acid catalysis to give the α-hydroxy acids (R)-3.This (R)-oxynitrilase also catalyzes the enantioselective addition in aqueous citrate buffer (50 mM, pH 4.0), as demonstrated for the preparation of (R)-methyl alkyl ketone cyanohydrins (R)-5 which are obtained in high enantiomeric excesses comparable to those in diisopropyl ether as solvent.