124-12-9

Basic information

• Product Name: OCTANENITRILE
• Synonyms: N-CAPRYLIC NITRILE;caprylic nitrile;Octannitril;Caprylonitrile, Heptyl cyanide;n-Heptyl cyanide,97%;Heptyl cyanide,Caprylonitrile;N-HEPTYL CYANIDE;N-OCTYL NITRILE
• CAS NO: 124-12-9
• Molecular Formula: C₈H₁₅N
• Molecular Weight: 125.21
• EINECS: 204-682-2
• Mol File: 124-12-9.mol
• Article Data: 156

Chemical Properties

• Melting Point: −45 °C(lit.)
• Boiling Point: 198-200 °C(lit.)
• Flash Point: 165 °F
• Appearance: /
• Density: 0.814 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.241mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• BRN: 1744063
• CAS DataBase Reference: OCTANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: OCTANENITRILE(124-12-9)
• EPA Substance Registry System: OCTANENITRILE(124-12-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• RIDADR: 3276
• WGK Germany: 2
• RTECS: RG9700300
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 124-12-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Different sources of media describe the Uses of 124-12-9 differently. You can refer to the following data:
1. Octanenitrile is a reagent often used in the preparation of amides by hydration using amorphous manganese oxide catalyst in the presence of reduced amounts of water.
2. Heptyl cyanide (Caprylonitrile) was used as a solvent to study the intermediates in the decomposition of aliphatic diazo-compounds.

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

• 4359-57-3 2-heptyl-1,3-dioxolane 
• 111-25-1 1-bromo-hexane 
• 75-05-8 acetonitrile 
• 124-11-8 non-1-ene 
• 4550-05-4 1-nitro-1-octene 
• 124-13-0 Octanal 
• 629-37-8 1-nitrooctane 
• 111-87-5 octanol 
• 111-86-4 n-Octylamine 
• 111-71-7 heptanal 
• 151-50-8 potassium cyanide 
• 1883-38-1 tripentylborane 
• 107-13-1 acrylonitrile 
• 420-04-2 CYANAMID 

Downstream Products

• 37622-68-7 1-(2,4-dihydroxyphenyl)octan-1-one 
• 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 
• 111-87-5 octanol 
• 124-13-0 Octanal 
• 34557-54-5 methane 
• 74-84-0 ethane 
• 74-98-6 propane 

Relevant articles and documents

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.

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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.

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.

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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.

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Preparation of nitriles from aldehydes using ammonium persulfate by means of a nitroxide-catalysed oxidative functionalisation reaction

A methodology for the preparation of nitriles from aldehydes by means of an oxidative functionalisation reaction is reported. It employs ammonium persulfate as both the primary oxidant and the nitrogen source, and a catalytic amount of a nitroxide. It is applicable to a range of structurally diverse (hetero)aromatic aldehydes furnishing the nitrile products in 30-97% isolated yield. Given the ready accessibility of aldehydes and that ammonium persulfate is cheap and less toxic than many other reagents for generating nitriles, this methodology offers a simple and easy to use approach to this valuable class of compounds. This journal is