Nonanenitrile

Base Information

• Chemical Name: Nonanenitrile
• CAS No.: 2243-27-8
• Molecular Formula: C9H17N
• Molecular Weight: 139.241
• Hs Code.: 2926909090
• European Community (EC) Number: 218-808-9
• NSC Number: 5560
• UNII: 6Q10KP3P20
• DSSTox Substance ID: DTXSID6022183
• Nikkaji Number: J46.553D
• Wikidata: Q27265303
• Mol file: 2243-27-8.mol

Synonyms:n-octyl cyanide;nonanenitrile

Chemical Property of Nonanenitrile

Chemical Property:

• Appearance/Colour: clear yellow to orange liquid
• Vapor Pressure: 0.0874mmHg at 25°C
• Melting Point: -35 °C
• Refractive Index: n20/D 1.426(lit.)
• Boiling Point: 225.2 °C at 760 mmHg
• Flash Point: 81.1 °C
• PSA: 23.79000
• Density: 0.816 g/cm³
• LogP: 3.26058
• Water Solubility.: Insoluble in water
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 139.136099547
• Heavy Atom Count: 10
• Complexity: 98.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

Nonanenitrile >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CCCCCCCCC#N
• General Description: N-OCTYL CYANIDE (also known as 1-Cyanooctane, Nonanitrile, Pelargonitrile, etc.) is an aliphatic nitrile used industrially as a solvent, intermediate, or precursor for surfactants and life sciences products. The enzymatic synthesis of such nitriles, including N-OCTYL CYANIDE, can be achieved at exceptionally high substrate loadings (up to 1.4 kg/L) using a heme protein biocatalyst, specifically an aldoxime dehydratase, which efficiently converts aldoximes into nitriles in a two-phase aqueous system with straightforward product isolation. This method demonstrates high productivity and scalability for industrial applications.

Technology Process of Nonanenitrile

There total 108 articles about Nonanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

n-Nonylamin (112-20-9) → nonanonitrile (2243-27-8)

Guidance literature:

With C₂₂H₂₂Cl₂FeN₂O₈^(2-)*2C₁₆H₃₆N⁽¹⁺⁾; oxygen; In neat (no solvent); at 100 ℃; for 0.5h; under 760.051 Torr; Green chemistry;

DOI:10.1016/j.tetlet.2015.12.082

Reference yield: 97.2%

1-Iodooctane (629-27-6) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → nonanonitrile (2243-27-8)

Guidance literature:

2-hydroxy-2-methylpropanenitrile; With lithium hydroxide monohydrate; In tetrahydrofuran; at 50 ℃; for 1h;

1-Iodooctane; In tetrahydrofuran;

Reference yield: 96.0%

nonan-1-al (124-19-6) → nonanonitrile (2243-27-8)

Guidance literature:

nonan-1-al; With triethylamine; In acetonitrile; at 0 - 20 ℃; for 0.5h;

With phthalic anhydride; In acetonitrile; for 16h; Reflux;

upstream raw materials:

n-chlorooctane

sodium cyanide

1-Iodooctane

potassium cyanide

Downstream raw materials:

4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

heptadecan-9-one

nonylamine hydrochloride

2-methylnonanenitrile

Refernces

Enzymatic Synthesis of Aliphatic Nitriles at a Substrate Loading of up to 1.4 kg/L: A Biocatalytic Record Achieved with a Heme Protein

10.1021/acs.joc.9b00184

The research focuses on the enzymatic synthesis of aliphatic nitriles, which are widely used as industrial bulk chemicals, solvents, and intermediates for the production of surfactants and life sciences products. The study aims to develop a biocatalytic approach that operates at high substrate loadings, up to an unprecedented 1.4 Kg/L, as demonstrated for the synthesis of n-octanenitrile. This substrate loading is one of the highest ever reported in biocatalysis and is the highest obtained for a water-immiscible product in an aqueous medium. The researchers used a recombinant aldoxime dehydratase from Bacillus sp. OxB-1 as a biocatalyst for the dehydration of aldoximes, which are readily available starting materials prepared from aliphatic aldehydes through spontaneous condensation with hydroxylamine. The process achieved excellent conversions towards nitriles in a two-phase system, with products easily separated from the reaction mixture without further purification. The conclusions highlight the potential of this biocatalytic process for the production of aliphatic nitriles at high substrate loadings, showcasing the biocatalyst's productivity and the simplicity of the product recovery process.