135415-89-3

Basic information

• Product Name: (R)-2-HYDROXY-2-METHYL-HEXANENITRILE
• Synonyms: (R)-2-HYDROXY-2-METHYL-HEXANENITRILE
• CAS NO: 135415-89-3
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18
• Mol File: 135415-89-3.mol

Chemical Properties

• Boiling Point: 231.9±13.0 °C(Predicted)
• Appearance: /
• Density: 0.941±0.06 g/cm3(Predicted)
• PKA: 11.45±0.29(Predicted)
• CAS DataBase Reference: (R)-2-HYDROXY-2-METHYL-HEXANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-HYDROXY-2-METHYL-HEXANENITRILE(135415-89-3)
• EPA Substance Registry System: (R)-2-HYDROXY-2-METHYL-HEXANENITRILE(135415-89-3)

Safety Data

• Hazardous Substances Data: 135415-89-3(Hazardous Substances Data)

Usage

Uses

Used in the Food and Beverage Industry:
(R)-2-Hydroxy-2-methyl-hexanenitrile is used as a flavoring agent for its fruity aroma, enhancing the taste and appeal of various food and beverage products.
Used in Pharmaceutical Production:
(R)-2-HYDROXY-2-METHYL-HEXANENITRILE is utilized in the production of pharmaceuticals, contributing to the development of new medications and therapeutic agents.
Used in Perfumes and Personal Care Products:
(R)-2-Hydroxy-2-methyl-hexanenitrile is employed as a fragrance in perfumes and personal care products, adding a pleasant scent to these items.
Used in Organic Synthesis and Chemical Production:
As a nitrile, (R)-2-hydroxy-2-methyl-hexanenitrile is involved in a wide range of applications in organic synthesis and chemical production, playing a crucial role in the creation of various chemical compounds and materials.
It is essential to handle (R)-2-hydroxy-2-methyl-hexanenitrile with care due to its potential hazardous properties and to adhere to proper safety protocols during its use.

Upstream product

• 74-90-8 hydrogen cyanide 
• 591-78-6 n-hexan-2-one 
• 38694-47-2 4-bromobutyraldehyde 
• 4111-12-0 (+/-)-2-methyl-2-hydroxyhexanenitrile 
• 1191-30-6 5-bromopentanal 

Relevant articles and documents

Synthesis of aliphatic and α-halogenated ketone cyanohydrins with the hydroxynitrile lyase from Manihot esculenta

The potential of the hydroxynitrile lyase from Manihot esculenta towards ketone substrates was investigated. It was observed that the length of the aliphatic chain is a key parameter for the conversion of aliphatic, non-branched ketones. Smaller substrates are readily converted with high enantioselectivites, but the elongation of the chain length causes a significant loss in enzyme activity. For a number of halogenated, herein especially fluorinated, acetophenone derivatives the corresponding cyanohydrins have been synthesized with good to moderate enantioselectivities. Overcoming limitations: Ketone cyanohydrins are extremely useful intermediates for the synthesis of unusual tertiary alcohols. In this contribution, the limits of the hydroxynitrile lyase from Manihot esculenta towards such substrates are investigated and evaluated. High enantioselectivities are obtained in a simple two-phase system, even with very challenging fluorinated acetophenone derivatives.

Enzyme-catalyzed Reactions, Part 39. A Convenient Synthesis of Optically Active 5,5-Disubstituted 4-Amino- and 4-Hydroxy-2(5H)-furanones from (S)-Ketone Cyanohydrins

(S)-Ketone cyanohydrins (S)-2 are accessible by enantioselective HCN addition to ketones 1 by using hydroxynitrile lyase from Manihot esculenta ((S)-MeHNL) as a biocatalyst. Acylation of (S)-2 gave the corresponding (S)-acyloxynitriles (S)-3, which can be cyclized by LHMDS to give 5,5-disubstituted (S)-4-amino-2(5 H)-furanones (S)-4 and (S)-5. Different substituents (H, Me, OBn, OH) in the 3-position of the furanones were introduced by selecting the appropriate acylating agent, which in the case of benzyloxyacetyl chloride led to the novel structure type of 4-amino-3-hydroxyfuranones (S)-5. For the synthesis of 5,5-disubstituted (S)-tetronic acids (S)-8, ketone cyanohydrins (S)-2 were first transformed into the corresponding 2-hydroxy esters (S)-6. Acylation of (S)-6 gave 2-acyloxy esters (S)-7, which, by treatment with LHMDS or LDA, afforded tetronic acids (S)-8 in high yields and enantiomeric excesses. By debenzylation of benzyloxy acetoxy derivatives (S)-8 e,f, the new vitamin C analogues (S)-9a,b were generated. All the described tetronic acid and aminofuranone derivatives were obtained in good chemical yields and without racemization with respect to the starting cyanohydrins (S)-2. ln many cases the enantiomeric purity could be enriched by simple recrystallization (e.g. (S)-4a from 69% ee to >99% ee).

Stereoselective substitution of (R)-2-(sulfonyloxy)nitriles with sulfur nucleophiles

Optically active 2-(4-toluenesulfonyloxy)-and (4- nitrobenzenesulfonyloxy)nitriles (R)-3 and (R)-4, which were obtained from (R)-cyanohydrins (R)-2 by sulfonylation, react with sulfur nucleophiles such as potassium thioacetate, potassium ethylxanthogenate, potassium thiocyanate, as well as thioalcohols and thiophenol in a typical S(N02 manner to give the (S)-2-sulfanyl nitriles (S)-7-9 and (S)-11-13 in good chemical yields and enantiomeric excesses. Even (R)-2-methyl-2-(methanesulfonyloxy)hexanenitrile (R)-6, derived from ketone cyanohydrin (R)-5, reacts with potassium thioacetate to yield (S)-2-acetylthio-2-methylhexanenitrile (S)-10 with 97% ee.

Enzymatic Synthesis of (R)-Cyanohydrins by Three (R)-Oxynitrilase Sources in Micro-aqueous Organic Medium

The enantioselective synthesis of optically active (R)-cyanohydrins generated from several aromatic, heteroaromatic and aliphatic aldehydes and methyl ketones was carried out using almond, peach or loquat meal as (R)-oxynitrilase sources in diisopropylether under micro-aqueous conditions The micro-aqueous reaction system, which is superior to the conventionally used water-organic biphase reaction system, performed well over the temperature range of 4 deg C to 30 deg C.

Synthesis of (R)-cyanohydrins by crude (R)-oxynitrilase-catalyzed reactions in micro-aqueous medium

In diisopropyl ether or ethyl acetate under micro-aqueous conditions, the enantioselective synthesis of (R)-cyanohydrins from aldehydes and methyl ketones was studied using crude (R)-oxynitrilase prepared from almonds. This reaction system performed well

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

Optically Active (S)-Ketone- and (R)-Aldehyde-cyanohydrins via an (R)-Oxynitrilase-catalysed Transcyanation. Chemoenzymatic Syntheses of 2-Cyanotetrahydrofuran and 2-Cyanotetrahydropyran

(R)-Oxynitrilase catalyses the enantioselective decyanation of racemic ketone cyanohydrins and the enantioselective addition of HCN to ω-bromoaldehydes in one step.

(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.