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

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

Uses

Used in Pharmaceutical Industry:
(S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE is used as a building block for the synthesis of various pharmaceuticals due to its unique chiral properties and reactivity, contributing to the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE serves as a key intermediate in the production of agrochemicals, such as pesticides and herbicides, leveraging its chemical reactivity and structural diversity to create effective and targeted products.
Used in Perfume Industry:
(S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE is used as an intermediate in the production of perfumes and flavoring agents, capitalizing on its ability to form a wide range of fragrant and flavorful compounds that can be used to create unique and appealing scents and tastes.
Used in Chemical Industry:
As a versatile compound, (S)-2-HYDROXY-2,4-DIMETHYL-PENTANENITRILE finds applications in various sectors of the chemical industry, where it is utilized as a starting material or intermediate for the synthesis of a diverse array of products, including specialty chemicals and advanced materials.

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

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

Enzyme catalysed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent system

By employing a vigorously stirred two phase system aqueous buffer/organic solvent and using the hydroxynitrile lyase from Hevea brasiliensis as biocatalyst enantiopure (S)-cyanohydrins from aliphatic, unsaturated, aromatic and heteroaromatic aldehydes and methyl alkyl and methyl phenyl ketones are obtained in high yield and in general 98-99% enantiomeric excess.

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.

Ueber die erste rekombinante Hydroxynitril-Lyase und ihre Anwendung in der Synthese von (S)-Cyanhydrinen

Keywords: Asymmetrische Synthesen; (S)-Cyanhydrine; Enzymkatalyse; Lyasen

(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.

Synthese und Reaktionen optisch aktiver Cyanhydrine

Bei der grossen Bedeutung, die Cyanhydrine in der Technik und in der Organischen Chemie immer schon hatten, ist es erstaunlich, dass optisch aktive Cyanhydrine erst in den letzten Jahren intensiver untersucht und in der Synthese eingesetzt wurden.Der Grund dafuer ist wohl darin zu sehen, dass es erst in neurerer Zeit gelungen ist, chirale Cyanhydrine, hauptsaechlich mit enzymatischen Methoden, relativ einfach und in hoher optischer Reinheit herzustellen.Chirale Cyanhydrine sind, zumeist als Glycoside geschuetzt, in der Natur weit verbreitet.Annaehernd dreitausend Pflanzen und vielen Insekten dienen sie unter anderem als Abwehrstoffe gegen "Fresser".Ihre grosse Bedeutung in der Organischen Chemie beruht auf ihrem enormen Synthesepotential fuer die Gewinnung anderer wichtiger chiraler Verbindungen.In Wirkstoffen sind chirale Cyanhydrinbausteine nur vereinzelt enthalten.Wegen der Notwendigkeit, bei neuen Wirksubstanzen mit Chiralitaetszentren, saemtliche Stereoisomere herzustellen und sie bezueglich ihres Wirkungsspektrums sowie ihres Metabolismus zu untersuchen, ist die Entwicklung neuer und einfacher stereoselektiver Synthesen erforderlich.Chirale Cyanhydrine koennen hierbei wertwolle Ausgangsverbindungen sein.Im vorliegenden Artikel werden folgende Themen behandelt: die durch die Enzyme (R)- oder (S)-Oxynitrilase katalysierte enantioselektive Addition von Blausaeure an Aldehyde und Ketone zu (R)- bzw. (S)-Cyanhydrinen; die durch cyclische Dipeptide katalysierte enantioselektive Addition von Blausaeure an Aldehyde; die durch Lipasen und Esterasen katalysierte enantioselektive Hydrolyse bzw.Veresterung racemischer Cyanhydrine und Cyanhydrinester; Folgereaktionen der Nitrilgruppe chiraler Cyanhydrine zu optisch aktiven α-Hydroxycarbonsaeuren, α-Hydroxyaldehyden, α-Hydroxyketonen und 2-Aminoalkoholen; Folgereaktionen der OH-Gruppe chiraler Cyanhydrine durch Sulfonylaktivierung und anschliessende stereoselektive Substitution mit Nucleophilen unter Konfigurationsumkehr zu optisch aktiven α-Azidonitrilen, α-Aminonitrilen unf α-Fluornitrilen.

Enzyme-catalyzed synthesis of (R)-ketone-cyanohydrins and their hydrolysis to (R)-α-hydroxy-α-methyl-carboxylic acids

(R)-Ketone-cyanohydrins (R)-2 are obtained with high enantioselectivity from aliphatic ketones 1 and HCN in organic solvents using (R)-oxynitrilase ( EC 4.1.2.10) as catalyst. Acid catalyzed hydrolysis of the cyanohydrins (R)-2 affords the corresponding (R)-α-hydroxy-α-methyl-carboxylic acids (R)-3 without measurable racemization.