124-12-9

Usage

Uses

Used in Chemical Synthesis:
Octanenitrile is used as a reagent for the preparation of amides by hydration, which is facilitated by an amorphous manganese oxide catalyst in the presence of reduced amounts of water. This application is particularly relevant in the chemical synthesis industry, where the production of amides is an important step in the synthesis of various compounds.
Used in Solvent Applications:
In the field of chemical research, Octanenitrile serves as a solvent for studying the intermediates in the decomposition of aliphatic diazo-compounds. Its solvent properties make it a valuable tool for understanding the reaction mechanisms and intermediates involved in these decomposition processes.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, Octanenitrile may also find applications in the pharmaceutical industry, potentially as an intermediate in the synthesis of various drugs or as a component in drug formulations due to its chemical properties and reactivity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 64, p. 3544, 1999 DOI: 10.1021/jo982317bTetrahedron Letters, 17, p. 255, 1976 DOI: 10.1016/S0040-4039(00)93701-8Chemical and Pharmaceutical Bulletin, 11, p. 296, 1963 DOI: 10.1248/cpb.11.296

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofNOx and CNí.

Purification Methods

Wash the nitrile twice with half-volumes of conc HCl, then with saturated aqueous NaHCO3, dry over MgSO4, filter and distil it. [Beilstein 2 H 349, 2 I 148, 2 II 303, 2 III 798, 2 IV 993.]

InChI:InChI=1/C8H15N/c1-2-3-4-5-6-7-8-9/h2-7H2,1H3

Upstream product

• 54244-10-9 1,3-diheptyl-thiourea 
• 629-01-6 n-octanamide 
• 13138-21-1 diazoacetonitrile 
• 1188-92-7 Trihexylboran; Tri-n-hexylbor 
• 111-86-4 n-Octylamine 
• 629-04-9 1-Bromoheptane 
• 13435-20-6 tetraethylammoniumcyanide 
• 111-85-3 n-chlorooctane 
• 420-04-2 CYANAMID 
• 623-66-5 octanoic acid anhydride 
• 1883-38-1 tripentylborane 
• 107-13-1 acrylonitrile 
• 4359-57-3 2-heptyl-1,3-dioxolane 
• 111-87-5 octanol 

Downstream Products

• 10436-11-0 bis-octanoylamino-methane 
• 6025-08-7 2,4-diamino-6-heptyl-1,3,5-triazine 
• 2876-58-6 1-n-octanoylnaphthalene 
• 37622-68-7 1-(2,4-dihydroxyphenyl)octan-1-one 
• 629-01-6 Caprylimidsaeure 
• 4219-47-0 ethylene glycol mono caprylate 
• 93340-36-4 3-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-2-heptyl-benzonitrile 
• 106-98-9 1-butylene 
• 187737-37-7 propene 
• 1116-76-3 Tri-n-octylamine 
• 111-86-4 n-Octylamine 
• 1120-48-5 n-dioctylamine 
• 10576-04-2 N-n-octylidene-n-octylamine 
• 93625-15-1 N-octyloctylamidine 

Relevant academic research and scientific papers

Iridium-catalyzed α-alkylation of acetonitrile with primary and secondary alcohols

Acetonitrile is successfully alkylated with primary and secondary alcohols in the presence of t-BuOK using [Ir(OH)- (cod)]2 as a catalyst. This method provides a very clean and atom-economical convenient direct route to substituted nitriles, which are very important raw materials in organic and industrial chemistry.

Heterogeneous Catalysts “on the Move”: Flow Chemistry with Fluid Immobilised (Bio)Catalysts

As both, continuous synthesis and (bio-)catalysis gained increasing interest in research as well as for industrial applications, ways for merging these fields enables novel opportunities for modern sustainable process development. In this contribution, an alternative approach for the application of immobilized enzymes in continuous flow processes is presented utilizing heterogeneous biocatalysts as a mobile phase. Based on superabsorber-entrapped enzymes and whole cells as a “fluid heterogeneous phase”, a segmented hydrogel/organic solvent system was developed. Its applicability was investigated with two entirely different model reaction systems, namely the alcohol dehydrogenase (ADH)-catalysed reduction of acetophenone, and the aldoxime dehydratase (Oxd)-catalysed dehydration of octanal oxime. In particular for solvent labile catalytic systems, this approach offers an alternative for the application of immobilized biocatalysts in a continuously running process beyond the “classic” packed bed and wall coated reactors.

Conversions of Carbonyl Compounds via Their Polymeric Sulfonylhydrazones into Alkenes, Alkanes, and Nitriles

Resins consisting of cross-linked poly(styrene-divinylbenzene) matrices functionalized with hydrazinosulfonyl groups react with aldehydes and ketones to form the sulfonylhydrazone derivatives.The extent of the reaction is sensitive to the type of resin and the bulk of the carbonyl compound.When heated strongly under alkaline conditions, the sulfonylhydrazones release the corresponding alkenes; upon the NaBH4 or LiAlH4 treatment, they also release the corresponding alkanes; and, upon refluxing in methanol with potassium cyanide, they release nitriles containing one additional carbon atom.

Stereoretentive Deuteration of α-Chiral Amines with D2O

We present the direct and stereoretentive deuteration of primary amines using Ru-bMepi (bMepi = 1,3-(6′-methyl-2′-pyridylimino)isoindolate) complexes and D2O. High deuterium incorporation occurs at the α-carbon (70-99%). For α-chiral amines, complete retention of stereochemistry is achieved when using an electron-deficient Ru catalyst. The retention of enantiomeric purity is attributed to a high binding affinity of an imine intermediate with ruthenium, as well as to a fast H/D exchange relative to ligand dissociation.

An elimination reaction of N-carbomethoxy-N,N-dimethylhydrazonium salts to alkyl nitriles

A new kind of elimination of hydrazonium salts to alkyl nitriles has been developed. The reaction of hydrazones and chloroformates results in the formation of hydrazonium salts, which react in situ with water to afford alkyl nitriles. The elimination is adapted to a range of solvents and gives good yields of α-secondary and tertiary alkyl-substituted nitriles.

Effect of Particle Wettability and Particle Concentration on the Enzymatic Dehydration of n-Octanaloxime in Pickering Emulsions

Pickering emulsion systems have emerged as platforms for the synthesis of organic molecules in biphasic biocatalysis. Herein, the catalytic performance was evaluated for biotransformation using whole cells exemplified for the dehydration of n-octanaloxime to n-octanenitrile catalysed by an aldoxime dehydratase (OxdB) overexpressed in E. coli. This study was carried out in Pickering emulsions stabilised solely with silica particles of different hydrophobicity. We correlate, for the first time, the properties of the emulsions with the conversion of the reaction, thus gaining an insight into the impact of the particle wettability and particle concentration. When comparing two emulsions of different type with similar stability and droplet diameter, the oil-in-water (o/w) system displayed a higher conversion than the water-in-oil (w/o) system, despite the conversion in both cases being higher than that in a “classic” two-phase system. Furthermore, an increase in particle concentration prior to emulsification resulted in an increase of the interfacial area and hence a higher conversion.

Biotransformations in Pure Organic Medium: Organic- Solvent-Labile Enzymes in the Batch and Flow Synthesis of Nitriles

In recent years, there has been an increasing tendency to use biocatalysts in industrial chemistry, especially in the pharma and fine chemical sector. Preferably, enzymes or whole cells, applied as catalysts for a specific biotransformation, are utilized in aqueous reaction media since water is the natural medium for enzymes. In numerous examples of biocatalytic systems, however, a major problem is the insolubility of hydrophobic substrates in such aqueous reaction media. Apart from lipases, many enzymes are highly sensitive to organic solvents and are inactivated by an organic medium. Therefore, a change of solvent for biotransformations from water to organic solvents is usually challenging. In this study, we investigated the synthesis of nitriles by an organic solvent-labile aldoxime dehydratase in pure organic solvents, exemplified for the dehydration of n-octanaloxime to n-octanenitrile. We present a method for applications in batch as well as flow mode based on an “immobilized aqueous phase” bearing the whole cells in a superabsorber as solid phase, thus enabling the use of a purely organic solvent as “mobile phase” and reaction medium.

One-step conversion of alcohols into nitriles with simultaneous two-carbon chain elongation. (Cyanomethyl)trimethylphosphonium iodide as a reagent with a dual mode of action

Treatment of alcohols with an excess of (cyanomethyl)trimethylphosphonium iodide leads, after aqueous hydrolysis, to the clean formation of nitriles with two more carbon atoms than present in the original alcohol. Benzylic, allylic, and aliphatic alcohols without β-branching (RCH2- CH2OH) have been converted to nitriles with success. The required phosphonium iodide is simple to prepare and can be stored for a long time at room temperature.

Segmented Flow Processes to Overcome Hurdles of Whole-Cell Biocatalysis in the Presence of Organic Solvents

In modern process development, it is imperative to consider biocatalysis, and whole-cell catalysts often represent a favored form of such catalysts. However, the application of whole-cell catalysis in typical organic batch two-phase synthesis often struggles due to mass transfer limitations, emulsion formation, tedious work-up and, thus, low yields. Herein, we demonstrate that utilizing segmented flow tools enables the conduction of whole-cell biocatalysis efficiently in biphasic media. Exemplified for three different biotransformations, the power of such segmented flow processes is shown. For example, a 3-fold increase of conversion from 34 % to >99 % and a dramatic simplified work-up leading to a 1.5-fold higher yield from 44 % to 65 % compared to the analogous batch process was achieved in such a flow process.

Conversion of aldoximes into nitriles with raney nickel in refluxing 2-propanol

Aldoximes are readily dehydrated to nitriles with Raney nickel in refluxing 2-propanol. Copyright Taylor & Francis Group, LLC.