10021-65-5

Basic information

• Product Name: [R,(+)]-2-Hydroxyhexanenitrile
• Synonyms: [R,(+)]-2-Hydroxyhexanenitrile
• CAS NO: 10021-65-5
• Molecular Formula: C6H11NO
• Molecular Weight: 0
• Mol File: 10021-65-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [R,(+)]-2-Hydroxyhexanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: [R,(+)]-2-Hydroxyhexanenitrile(10021-65-5)
• EPA Substance Registry System: [R,(+)]-2-Hydroxyhexanenitrile(10021-65-5)

Safety Data

• Hazardous Substances Data: 10021-65-5(Hazardous Substances Data)

Usage

General Description

"[R,(+)]-2-Hydroxyhexanenitrile", also known as R-2-Hydroxyhexanenitrile, is a chemical compound with a molecular formula of C6H11NO. It falls under the category of nitriles, which are organic compounds with a -C≡N functional group. The R- and (+) in its name indicate its absolute stereochemistry and its optical rotation, respectively. [R,(+)]-2-Hydroxyhexanenitrile, being chiral, can exist in two different forms, which are isomers of each other. It is generally used in niche scientific research, often in the field of synthetic chemistry for potential applications in pharmaceuticals and other chemical products.

Upstream product

• 110-62-3 pentanal 
• 74-90-8 hydrogen cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 64350-07-8 2-hydroxyhexanenitrile 

Relevant articles and documents

Synthesis of the bifunctional BINOL ligands and their applications in the asymmetric additions to carbonyl compounds

Efficient one-step syntheses of the bifunctional BINOL and H8BINOL ligands (S)-6 and (S)-8 have been developed from the reaction of BINOL and H8BINOL with morpholinomethanol, respectively. The X-ray analyses of these compounds have revealed their structural similarity and difference. The bifunctional H8BINOL (S)-8 is found to be highly enantioselective for the reaction of diphenylzinc with many aliphatic and aromatic aldehydes and especially is the most enantioselective catalyst for linear aliphatic aldehydes. Unlike other catalysts developed for the diphenylzinc addition which often require the addition of a significant amount of diethylzinc with cooling (or heating) the reaction mixture in order to achieve high enantioselectivity, using (S)-8 needs no additive and gives excellent results at room temperature. (S)-8 in combination with diethylzinc and Ti(OiPr)4 can catalyze the highly enantioselective phenylacetylene addition to aromatic aldehydes. It can also promote the phenylacetylene addition to acetophenone at room temperature though the enantioselectivity is not very high yet. Without using Ti(OiPr)4 and a Lewis base additive, (S)-8 in combination with diethylzinc can catalyze the reaction of methyl propiolate with an aldehyde to form the highly functional γ-hydroxy-α,β-acetylenic esters except that the enantioselectivity is low at this stage. The bifunctional BINOL ligand (S)-6 in combination with Me2AlCl is found to be a highly enantioselective catalyst for the addition of TMSCN to both aromatic and aliphatic aldehydes.

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

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

Enzyme-Catalysed Synthesis of Optically Active Aliphatic Cyanohydrins

The enantioselective preparation of aliphatic (R)-cyanohydrins was studied using powdered almond meal, a rich source of mandelonitrile lyase, as a catalyst in organic solvent.The feasibility of powdered almond meal as a catalyst was compared to that of a purified enzyme preparation.